Insecticidal substituted indazoles

ABSTRACT

Certain substituted indazoles, including all geometric and stereoisomers thereof, agricultural compositions containing the indazoles and use of the indazoles as insecticides.

CROSS-REFERENCE TO RELATED APPLICATION

This application is a continuation of U.S. Ser. No. 159,763 filed onMar. 8, 1988, now abandoned, which in turn is a continuation-in-part ofU.S. Ser. No. 036.480, filed on Apr. 9, 1987, now abandoned.

BACKGROUND OF THE INVENTION

1. FIeld of the Invention

This invention pertains to substituted agricultural compositionscontaining them and a method for using the indazoles to control insects.

2. State of the Art

U.S. Pat. No. 4,070,365 discloses insecticidal compounds of the formula##STR1## wherein R₂ and R₃ are independently alkyl, cycloalkyl, pyridylor thienyl optionally substituted with halogen, alkyl or nitro, or aphenyl group optionally substituted with 1 or 2 substituents selectedfrom halogen, alkyl, haloalkyl, cycloalkyl, alkylthio, alkoxy, mono ordialkylamino, nitro, phenyl optionally substituted with halogen, orcyano;

Y is halogen, NO₂, alkyl, haloalkyl, cycloalkyl, alkylthio, alkoxy,dialkylamino alkylsulfonyl, acyl, acylamino, cyano, or a phenyloptionally substituted with halogen; and

X is O or S.

U.S. Pat. No. 4,663,341 discloses insecticidal compounds of the formula##STR2## wherein A is unsubstituted or substituted phenyl;

B is unsubstituted or substituted phenyl;

U is O, S or NR;

Y is alkyl, carbonyl or phenyl each of which may be optionallysubstituted; and

Z is an organic radical other than hydrogen.

SUMMARY OF THE INVENTION

This invention pertains to compounds of Formula I, including allgeometric and stereoisomers, agriculturally suitable salts thereof,agricultural compositions containing them and their use as insecticides:##STR3## wherein ##STR4## A is a 1. 2 or 3-atom bridge having 0 to 3carbon atoms and 0 to 1 oxygen atom, NR₆ group, or S(O)_(q) group,wherein each carbon individually can be substituted with 1 to 2substituents selected from 1 to 2 halogen, C₁ to C₆ alkyl C₂ to C₄alkoxycarbonyl or phenyl optionally substituted with 1 to 3 substituentsselected from W and one of the carbon atoms can be C(O) or C(S);

B is H, C₁ to C₆ alkyl, C₁ to C₆ haloalkyl, C₂ to C₆ alkenyl, C₂ to C₆haloalkenyl, C₂ to C₆ alkynyl, OR₇, C₂ to C₆ alkoxyalkyl, C₂ to C₆cyanoalkyl, C₃ to C₈ alkoxycarbonylalkyl, CO₂ R₃, C(O)R₃, C(O)NR₃ R₄,C(S)NR₃ R₄, C(S)R₃, C(S)SR₃, phenyl, phenyl substituted by (R₅)_(p),benzyl, or benzyl substituted with 1 to 3 substituents indePendentlyselected from W;

J is H, C₁ to C₄ alkyl or phenyl optionally substituted with W;

K is H or CH₃ ;

W is halogen, CN, NO₂, C₁ to C₂ alkyl, C₁ to C₂ haloalkyl, C₁ to C₂alkoxy, C₁ to C₂ haloalkoxy, C₁ to C₂ alkylthio, C₁ to C₂ haloalkylthio,C₁ to C₂ alkylsulfonyl or C₁ to C₂ haloalkylsulfonyl;

R₁, R₂ and R₅ are independently R₃, halogen, CN, N₃, SCN, NO₂, OR₃, SR₃,SOR₃, SO₂ R₃, OC(O)R₃, OSO₂ R₃, CO₂ R₃, C(O)R₃, C(O)NR₃ R₄, SO₂ NR₃ R₄,NR₃ R₄, NR₄ C(O)R₃, OC(O)NHR₃, NR₄ C(O)NHR₃, NR₄ SO₂ R₃, or when m, n orp is 2, R₁, R₂ or R₅ can be taken together to form a 5 or 6 memberedfused ring as --OCH₂ O--, --OCH₂ CH₂ O--, or --CH₂ CH₂ O--, each ofwhich can be substituted with 1 to 4 halogen atoms or 1 to 2 methylgroups;

R₃ is H, C₁ to C₆ alkyl, C₁ to C₆ haloalkyl, C₂ to C₆ alkenyl, C₂ to C₆haloalkenyl, C₂ to C₆ alkynyl, C₂ to C₆ haloalkynyl, C₂ to C₆alkoxyalkyl, C₂ to C₆ alkylthioalkyl, C₁ to C₆ nitroalkyl , C₂ to C₆cyanoalkyl, C₃ to C₈ alkoxycarbonylalkyl, C₃ to C₆ cycloalkyl, C₃ to C₆halocycloalkyl, phenyl, benzyl, or phenyl or benzyl substituted with 1to 3 substituents independently selected from W;

R₄ is H, C₁ to C₄ alkyl or R₃ and R₄ can be taken together as (CH₂)₄,(CH₂)₅ or (CH₂ CH₂ OCH₂ CH₂);

R₆ is H, C₁ to C₄ alkyl, C₁ to C₄ haloalkyl, C₂ to C₄ alkenyl, C₂ to C₄haloalkenyl, phenyl, benzyl, phenyl optionally substituted with W orbenzyl optionally substituted with W;

R₇ is H, C₁ to C₄ alkyl, C₂ to C₄ alkenyl,

C₂ to C₄ alkynyl, C₂ to C₄ alkylcarbonyl,

C₂ to C₄ alkoxycarbonyl, C₁ to C₄ alkylsulfonyl;

X is O or S;

n is 1 to 4;

m is 1 to 5;

p is 1 to 3;

q is 0 to 2; and

Y is H, C₁ to C₆ alkyl, benzyl, C₂ to C₆ alkoxyalkyl, CHO, C₂ to C₆alkylcarbonyl, C₂ to C₆ alkoxycarbonyl, C₂ to C₆ haloalkylcarbonyl, C₁to C₆ alkylthio, C₁ to C₆ haloalkylthio, phenylthio, or phenylthiosubstituted with 1 to 3 substituents independently selected from W.

Preferred compound (A) are those of Formula I wherein Q is ##STR5## X isO or S; X¹ is O or S;

t is 0, 1 or 2;

V is O, S(O)_(q), or NR₆ ;

Z is O or NR₆.

R₈ is H, halogen, C₁ -C₆ alkyl, C₂ -C₄ alkoxycarbonyl, phenyl or phenylsubstituted by 1-3 substituents selected from W; and

g is 0, 1 or 2.

Preferred compounds (B) are preferred compounds (A) wherein

B is H, C₁ to C₆ alkyl, C₁ to C₆ haloalkyl, C₂ to C₆ alkenyl, C₂ to C₆alkynyl, C₂ to C₆ alkoxyalkyl, C₃ to C₈ alkoxycarbonylalkyl, CO₂ R₃,C(O)R₃, C(O)NR₃ R₄, C(S)NR₃ R₄, C(S)R₃, C(S)SR₃, phenyl or phenylsubstituted by (R₅)_(p) ;

J is H or CH₃ ;

R₃ is H, C₁ to C₄ alkyl, C₁ to C₂ haloalkyl, C₃ to C₄ alkenyl, C₃ to C₄haloalkenyl, propargyl, phenyl, benzyl, or phenyl or benzyl substitutedwith one of F, Cl, Br, CF₃ or NO₂ ;

R₆ is H, C₁ to C₄ alkyl, allyl or propargyl;

n is 1 or 2;

P is 1 or 2;

m is 1 to 3; and

Y is H, C₁ to C₄ alkyl, SCH₃, SCCl₃, SO₂ CH₃, SC₆ H₅, 2--NO₂ --C₆ H₄ S,C(O)CH₃, C(O)CF₃ ; CO₂ CH₃ or CO₂ CH₂ CH₃.

Preferred compounds (C) are preferred compounds (B) wherein

B is H, C₁ to C₄ alkyl, C₃ -C₄ alkoxycarbonylalkyl, CO₂ R₃, C(O)R₃,phenyl or phenyl substituted by (R₅)_(p) ;

J is H;

K is H;

R₁ is H, halogen, CN, SCN, NO₂, OR₃, SR₃, SO₂ R₃, CO₂ R₃, C(O)R₃ or R₃with one R₁ substituent in the 4-position, or when m is 2 then R₁ can betaken together as --CH₂ C(CH₃)₂ O--, OCH₂ CH₂ O--, OCF₂ CF₂ O-- or --CF₂CF₂ O-- to form a 5 or 6 membered fused ring;

R₂ and R₅ are H, R₃, halogen, CN, SCN, NO₂, OR₃, SR₃, SO₂ R₃, OC(O)R₃,OSO₂ R₃, CO₂ R₃, C(O)R₃, C(O)NR₃ R₄, SO₂ NR₃ R₄ or NR₃ R₄ ;

R₃ is C₁ -C₄ alkyl, C₁ -C₂ haloalkyl C₃ -C₄ alkenyl or propargyl;

R₄ and R₈ are H or CH₃ ;

X is 0;

X' is 0;

m is 1 or 2;

t is 1; and

q is 0.

Preferred compounds (D) are preferred compounds (C) wherein

R₁ is Cl, F, Br, CF₃, CN, OCF₃, OCF₂ H or SCF₂ H;

R₂ is H, Cl, F, Br, CN, CF₃, CH₃, OCF₂ H, OCF₃, SCH₃, SCF₂ H, SO₂ CH₃ orNO₂ ;

R₆ is H or CH₃ ;

B is H, CH₃, CH₂ CH₃, CO₂ CH₃, CO₂ CH₂ CH₃, phenyl or phenyl substitutedby halogen, CN, CF₃ or NO₂, and;

Y is H.

Preferred compounds (E) are preferred compounds (D) wherein

Q is Q-1.

Preferred compounds (F) are preferred compounds (D) wherein

Q is Q-2;

Specifically preferred compounds are preferred compounds (E):

Methyl3,3a,4,5-tetrahydro-2-[[4-(trifluoromethyl)phenylamino]carbonyl]-2H-benz[g]indazole-3a-carboxylate.(G)

Methyl7-chloro-3,3a,4,5-tetrahydro-2-[[4-trifluoromethyl)phenylamino]carbonyl]2H-benz[g]indazole-3a-carboxylate,(H)

7-Chloro-3,3a,4,5-tetrahydro-N-[4-(trifluoromethyl)phenyl]-2H-benz[g]indazole-2-carboxamide,(I)

Methyl6-fluoro-3,3a,4,5-tetrahydro-2-[[4-(trifluoromethyl)phenylamino]carbonyl]-2H-benz[g]indazole-3a-carboxylate,(J).

The compound of this invention, in addition to being useful as foliarand/or soil insecticides, can be combined with other pesticides foragricultural uses that will readily occur to one skilled in the art.Reference to compounds of this invention or to compounds of Formula Iincludes geometric and stereoisomers thereof as well as agriculturallysuitable salts which, for brevity only, are not referred to specificallyhereafter.

DETAILS OF THE INVENTION

For descriptive purposes, the following numbering system will be used todescribe the values of Q in both the discussion and tables that follow.##STR6##

Compounds of Formula I can be prepared by the reaction of arylisocyanates of Formula II and substituted indazoles of Formula III asshown in Scheme I. Typical reactions involve the combination ofequimolar amounts of II and III in conventional organic solventsincluding ether, tetrahydrofuran (THF), methylene chloride, chloroformand benzene, The reaction can be run at temperatures ranging from about-20° C. to 100° C. with temperatures in the range of about -10° to 30°C. generally preferred. ##STR7##

Substituted indazoles of Formula III, where B is equal to H, can beprepared by the reaction of hydrazine with an α, β-unsaturated ketone ofFormula IV (or their precursors) by procedures well documented in thechemical literature (Scheme 2). For a review of pyrazoline synthesis,see El-Rayyes and Al-Awadi. Synthesis, 1028 (1985). For literaturedescribing the synthesis of 3,4- and 3,5-disubstituted pyrazolines,which can be applied to the synthesis of compounds of Formula III, whereB is H, see U.S. Pat. 3,991,073 and U.S. Pat. 4.070.365. ##STR8##

Preparation of compounds of Formula I, where B is other than H, OR₇phenyl or substituted phenyl can be achieved by metallation of the 3a-position of Formula I (where B is H) followed by reaction with asuitable electrophile as depicted in Scheme 3. Procedures for therelated transformation of 4-substituted pyrazolines to 4,4-disubstitutedpyrazolines are reported in European patent application No. 153127 andcan be applied to substituted indazoles of Formula I. Metallation can beaccomplished by deprotonation with a strong base, in a suitable solventand at temperatures ranging from -78° C. to 100° C. Useful base for thisreaction includes lithium dialkylamides such as lithium diisopropylamideand lithium tetramethylpiperide, alkyl lithium reagents such asn-butyllithium and metal hydrides such as sodium hydride and potassiumhydride. Deprotonation of compounds of Formula I, where B is equal tohydrogen, may require two equivalents of base when Y is equal tohydrogen. The reaction can be conducted in many conventional organicsolvents and in certain instances a cosolvent may be useful. Suitablesolvents include diethylether, tetrahydrofuran, tetrahydropyran,dimethylformamide, hexamethylphosphoramide, benzene and the like.Suitable electrophilic reagents for reaction with the metallated FormulaI compounds include alkyl and substituted alkyl halides, alkylchloroformates, acyl halides, isocyanates, dialkyl carbamoylhalides andrelated electrophiles which will be known to those skilled in the art.##STR9## Where E⁺ is an electrophilic reagent.

An alternative Procedure for introduction of the 3a-substituent, whichin certain instances may be preferred over that of scheme 3 due tohigher yields and/or greater ease of synthesis. Proceeds via theintermediacy of compound V, wherein the 2-nitrogen has been derivatizedwith a suitable protecting group. Deprotonation with a strong base suchas lithium diisopropylamide, typically in stoichiometric quantities,followed by reaction with any of the previously described electrophilesprovides compounds of Formula V where B is other than hydrogen, OR₇,phenyl or substituted phenyl. Removal of the nitrogen protecting groupprovides the required Formula III intermediate. Nitrogen-protectinggroups are well documented in the chemical literature, as are proceduresfor their preparation and cleavage. Examples include acetyl,trifluoroacetyl, benzoyl, substituted benzoyl, alkoxycarbonyl, benzyland substituted benzyl. For a review see Greene "Protective Groups inOrganic Synthesis" New York: John Wiley and Sons, 1981) pp. 218 to 287.##STR10## where E⁺ is an electrophile and PG is representative of asuitable nitrogen-protecting group.

Formula III compounds where B is equal to hydroxy are prepared by thereaction of hydrazine with a suitably substituted epoxide of Formula VI(Scheme 5, Reaction 1). The epoxides are available from the enones ofFormula IV by Procedures known in the art, the most widely employedmethod being epoxidation via the use of alkaline hydrogen peroxide (see,e.g., Wasson and House, Org. Syn., Coll. Vol. 4, 552 (1963)).

Compounds of Formula III where B is equal to OR₇ and R₇ is other thanhydrogen, may be prepared from the Formula III compounds where B isequal to hydroxy via reaction with electrophilic reagents such as alkylhalides, acyl halides, alkyl chloroformates. chlorosulfonates,isocyanates and dialkyl carbamoylhalides (Scheme 5, Reaction 2). Thoseskilled in the art will recognize that conditions necessary for thistransformation including solvent, catalyst, temperature, etc., will varywith the specific electrophile chosen and that protection of the2-nitrogen may be necessary. ##STR11## where E⁺ and PG are as previouslydefined.

Compounds of Formula III where B is phenyl or substituted phenyl may beprepared by reaction of a substituted ketone of Formula VIII withhydrazine. The Formula VIII compounds are in turn prepared fromcompounds of Formula VII in a two-step process involving first an aldolor Mannich type reaction on the Formula VII compound followed byconversion of the hydroxyl or dialkylamino group to a leaving group L,examples of which include conversion to the chloride, bromide, tosylateor mesylate by procedures well known in the art. ##STR12##

Compounds of Formula IV (or their precursors) are readily prepared fromcompounds of Formula IX via an aldol condensation followed bydehydration of the aldol, or when J and K are hydrogen via a Mannichreaction followed by elimination of the dialkylamino group. For ageneral review of these reactions, see March, "Advanced OrganicChemistry", 3rd ed., (New York: John Wiley and Sons, 1985) pp. 829 to834, and House, "Modern Synthetic Reactions", 2nd ed., (Menlo Park. CA:N. A. Benjamine, 1972) pp. 655 to 660. ##STR13##

Those skilled in the ar twill recognize the intermediates of Formula IX,which include compounds such as indanones, tetralines, chromanones,thiochromanones, and the like are well documented in the chemicalliterature as are procedures for their preparation. Selected examples ofFormula IX are available commercially as well. The following Examplesfurther illustrate the invention.

EXAMPLE 1 3,3a,4,5-Tetrahydro-N-[4-trifuloromethyl)phenyl]-2H-benz[z]indazole-2-carboxamide

A mixture of 10.0 g of α-tetralone, 2.0 g of paraformaldehyde, 6.5 g ofdimethylamine hydrochloride and 1.75 ml of conc. HCl in 20 ml of ethanolwas heated at reflux for 24 h, cooled to room temperature and thenpartitioned between ether and water. The aqueous extracts were madebasic with 1N aqueous NaOH and extracted with ether. The ether extractswere dried over magnesium sulfate and concentrated to 12.3 g of a yellowoil. The residual oil was dissolved in 40 ml of n-propyl alcohol,combined with 6.7 ml of hydrazine hydrate and heated at reflux for 1 h.The reaction mixture was then concentrated under vacuum, partitionedbetween 5% aqueous NaHCO₃ and methylene chloride and dried overmagnesium sulfate. To the methylene chloride extracts were added 12.5 gof 4-trifluoromethylphenyl isocyanate and the mixture was then refluxedone hour, cooled to room temperature and concentrated to 26.1 g of abrown oil. Chromatography on silica gel followed by trituration withether afforded 11.78 g of the title compound as a tan powder, m.p.149°-151° C. ¹ H NMR (CDCl₃), δ 1.9 (m,1H), 2.4 (m,1H), 3.0 (m,2H), 4.4(m,1H), 7.3 (m,3H), 7.58 (d,2H), 7.65 (d,2H), 8.0 (d,2H), 8.3 (bs,1H).

EXAMPLE 23.3a,4,5-tetrahydro-3a-methyl-N-[4-(trifluoromethyl)phenyl]-2H-benz[q]indazole-2-carboxamide

To a solution of 0.9 ml of diisopropylamine in 10 ml of THF, at -78° C.,was added 2.3 ml of 2.5 M n-butyl lithium in hexane and the mixture wasstirred for 5 mins. To this -78° C. solution was added a solution of 1.0g of the title compound of Example 1 in 5 ml of THF. The reaction waswarmed to 0° C. recooled to -78° C. and then 0.4 ml of methyl iodide wasadded. The reaction mixture was then stirred for 24 h, with gradualwarming to room temperature, quenched with 0.5 ml of glacial aceticacid, and poured into a 5% solution of aqueous NaHCO₃. The mixture wasextracted with chloroform, dried over magnesium sulfate andconcentrated. Crystallization from 1:1 ethylacetate/hexane afforded 0.41g of a yellow solid, m.p. 130° to 135° C. Chromatography of the filtrateon silica gel with 30% ethyl acetate hexane afforded an additional 0.17g of a higher purity sample of the title compound, m.p. 152.5° to153.5°C. ¹ H NMR (CDCl₃), δ 1.29 (s, 3H), 2.1 (m,2H), 2.9-3.3 (m, 2H),3.70 (d, 1H), 4.12 (d,1H), 7.3 (m,3H), 7.57 (d,2H). 7.68 (d,2H), 7.98(d,1H), 8.3 (bs,1H).

EXAMPLE 3 Methyl3,3a,4,5-tetrahydro-2-[[4-(trifluoromethyl)phenylamino]carbonyl]-2H-benz[g]indazole-3a-carboxylate

Application of the procedure of Example 2 with 0.75 ml of methylchloroformate afforded, after chromatography on silica gel, 0.25 g ofthe title compound as a white solid m P. 177° to 180° C. ¹ H NMR(CDCl₃), δ 2.1 (m,1H), 2.7 (m,1H), 3.0 (m,2H), 3.71 (s,3H), 3.76 (d,1H),4.58 (d,1H), 7.3 (m,3H), 7.57 (d,2H), 7.66 (d,2H), 8.0 (d,1H), 8.22(s,1H),

EXAMPLE 47-Chloro-3,3a,4,5-tetrahydro-N-[4-(trifluoromethyl)phenyl]-2H-benz[g]indazole-2-carboxamide

Step A: ((2-(3-chlorophenyl)ethyl)methanesulfonate

To a 0° C. solution of 30.0 g of 3-chlorophenethyl alcohol and 15.3 mlof methane sulfonyl chloride in 150 ml of THF was added, dropwise, asolution of 28.0 ml of triethylamine in 50 ml of THF. The reaction waswarmed to room temperature, stirred overnight, and then filtered. Thefiltrate was partitioned between aqueous sodium bicarbonate and ether.The organic extracts were then dried over magnesium sulfate, filteredconcentrated under reduced pressure to afford 45.93 g of a clear,colorless oil. ¹ NMR was consistent with the structure for Step A.

Step B: 3-chlorobenzenebutanoic acid

To a mixture of 8.0 g of 60% sodium hydride in 300 ml of THF, under N₂,was added dropwise a solution of 31.0 ml of diethyl malonate in 50 ml ofTHF. Upon complete addition of the diethyl malonate, a pale yellowhomogenous solution was obtained. To this was added a solution of 45.93g of the sulfonate from Step A and the mixture was then heated at refluxovernight. The reaction was then cooled to room temperature, poured into400 ml of 1N HCl, and extracted with ether. The ether extracts weredried over magnesium sulfate, filtered and concentrated under reducedpressure to afford 68.9 g of a yellow oil. The crude oil was dissolvedin 400 ml of methanol, 100 ml of H₂ O and 40 ml of 50% aqueous NaOH. Thereaction was stirred overnight and the methanol was then removed atreduced pressure. The crude residue was partitioned between H₂ O andether, the aqueous extracts were acidified with concentrated HCl andthen extracted several times with ether. The ether extracts were driedover magnesium sulfate, filtered and concentrated to afford 51.7 g of ayellow oil. The crude residue was dissolved in 200 ml of toluene andheated at reflux for 4 days under N₂ to effect decarboxylation. Afterthis time toluene was removed by concentration at reduced pressure toafford 35.72 g of a yellow oil. ¹ H NMR analysis of the crude productwas consistent with 3-chlorobenzenebutanoic acid of purity estimated tobe 80%. The crude product was used without further purification directlyin the next step.

Step C: 6-chloro-3,4-dihydro-1-(2H)-naphthalenone

A mixture of 35.72 of the product from Step B and 50 ml of thionylchloride was heated at reflux for 2 hours and then stirred at roomtemperature for 18 hrs. After this time thionyl chloride was removed atreduced pressure and the product was dissolved in carbon tetrachlorideand concentrated at reduced pressure. The residue was dissolved in 150ml of dichloroethane cooled to 0° C. and 28 g of aluminum chloride wasadded portionwise over about 1 hr in approximately 3 g portions. Afterstirring for 3 hrs the reaction was poured over a mixture of ice/1N HCland extracted three times with methylene chloride. The organic extractswere dried over magnesium sulfate and concentrated to approximately 30 gof a brown oil. Chromatography on silica gel with 10% ethylacetate/hexane afforded 17.83 g of6-chloro-3,4-dihydro-1(2H)-naphthalenone as a brown oil. ¹ H NMR wasconsistent with the structure.

Step D:7-chloro-3,3a,4,5-tetrahydro-N-[4-(trifluoromethyl)phenyl]2H-benz[g]indazole-2-carboxamide

A mixture of 6-chloro-3,4-dihydro-1(2H)naphthalenone (Step C), 2.5 g ofdimethylamine hydrochloride, 1.0 g of paraformaldehyde, 0.7 ml ofconcentrated HCl and 15 ml of ethanol was combined and heated at refluxfor 18 hours. The reaction was then concentrated at reduced pressure andpartitioned between H₂ O and ether. The aqueous extracts were made basicwith 1N NaOH and then extracted three times with ether. The etherextracts were dried over magnesium sulfate and concentrated to 4.64 g ofa yellow oil. This compound was dissolved in 25 ml of ethanol and 1.5 mlof hydrazine hydrate was added followed by 5 to 6 drops of 50% solutionhydroxide. The reaction was then heated at reflux, under N₂, for 2 to 3hrs after which time it was cooled and most of the ethanol was removedby concentration at reduced pressure. The crude residue was partitionedbetween saturated aqueous sodium bicarbonate and methylene chloride. Themethylene chloride extracts were dried over magnesium sulfate andfiltered. The methylene chloride extracts were then combined with 3.5 gof 4-trifluoromethylphenyl isocyanate and stirred under N₂ overnight.The reaction was then concentrated and the crude residue triturated withether to afford 3.35 g of the title compound as a white powder, m.p.196° to 199° C. ¹ H NMR(CDCl₃) δ 1.9 (m, 1H), 2.2 (m, 1H), 3.0 (m, 2H),3.5 (m, 2H), 4.43 (m, 1H), 7.24 (m, 2H), 7.55 (d, 2H), 7.67 (d, 2H),7.92 (d, 1H), 8.20 (s, 1 H).

EXAMPLE 5 Methyl7-chloro-3,3a,4,5-tetrahydro-2-[[4(trifluoromethyl)phenylamino]carbonyl]-2H-benz[g]-indazole-3a-carboxylate

A solution of 50 ml of THF and 6.7 ml of diisopropylamine was cooledunder N₂ to -78° C. and then 17.5 ml of 2.5 M n-butyllithium in hexanewas added. After 5 min. a solution of 7.8 g of the title compound ofExample 4 in 15 ml of THF was added dropwise and the dark red solutionthat formed was stirred at -78° C. for an additional 15 min. After thistime a solution of 4.6 ml of methyl chloroformate in 10 ml of THF wasadded dropwise and the red color dissipated rapidly. The reaction waswarmed to room temperature and after 1 hr quenched with 5% aqueoussodium bicarbonate. The reaction mixture was partitioned between etherand 5% aqueous sodium bicarbonate. The ether extracts were dried overmagnesium sulfate and concentrated to 14.1 g of a yellow oily solid. Thecrude product was triturated with ether and the resulting whiteprecipitate was filtered and dried to afford 5.56 g of the titlecompound as a white solid, m.p. 234° C. to 236° C. ¹ H NMR(CDCl₃) δ 2.1(m, 1H), 2.75 (m, 1H) 2.95 (m, 2H), 3.71 (s, 3H), 3.75 (d, 1H, J=6Hz),4.59 (d, 1H, J=6Hz), 7.25 (m, 2H), 7.57 (d, 2H), 7.66 (d, 2H), 7.94 (d,1H), 8.18 (d, 1H),

EXAMPLE 67-chloro-2,3,3a,4-tetrahydro-N-[4-(trifluoromethyl)phenyl]-[1]benzothiodyrano[4.3-c]pyrazole-2-carboxamide

Step A:7-chloro-3-[(dimethylamino)methyl]-2,3-dihydro-4H-1-benzothiopyran-4-one

A mixture of 15.0 g (75.7 mmol) of 7-chlorothiochroman-4-one (Chu etal., Hua Hsueh Hsueh Pao. 1956, 22, 371-8; Chem. Abstracts. 1958, 52,11044a). 7.41 g 190.8 mmol) of dimethylamine hydrochloride. 3.41 g (113mmol) of paraformaldehyde, and 1.26 ml (15 mmol) of concentrated HCl in25 ml of ethanol under a nitrogen atmosphere was heated under reflux for22 hrs. The reaction mixture was poured into 150 ml of water andextracted with ether (2×50 ml). The aqueous layer was made basic (pH 10)with 1N NaOH and then was extracted with ethyl acetate (3×100 ml ).After being dried (MgSO₄), these ethyl acetate extracts wereconcentrated under reduced pressure to give 14.9 g of a yellow solid.The ¹ H NMR was consistent with the structure for the title compound.

Step B:7-chloro-2,3,3a,4-tetrahydro-N-[4-(trifluoromethyl)phenyl]-[1]benzothiopyrano[4,3-c]pyrazole-2-carboxamide

To a stirred mixture of 14.0 g (54.7 mol) of the Mannich base from StepA and 6.19 ml (6.38 g, 110 mmol) of hydrazine hydrate in 36 ml ofn-propanol under a nitrogen atmosphere was added 0.29 ml (5.5 mmol) of50% aqueous NaOH and the resulting mixture was heated at 100° C. for 2hrs. The reaction mixture was concentrated under reduced pressure,diluted with 250 ml of dichloromethane, and washed with 200 ml of diluteaqueous sodium bicarbonate. The aqueous layer was extracted with 50 mlof dichloromethane. The combined organic layers were dried (MgSO₄) andfiltered to give 370 ml of solution. A 120 ml portion of this solutionwas treated under a nitrogen atmosphere with 3.75 g (20.0 mmol) of4-(trifluoromethyl)pbenyl isocyanate and allowed to stir overnight. Thereaction mixture was concentrated under reduced pressure, and theresidue was triturated with 35 ml of ether and filtered to give 4.51 g(63%) of the title compound as a yellow solid melting at 188° to 192° C.¹ H NMR (CDCl₃, 200 MHz) δ 3.19 (dd, 4.5 Hz, 12.6 Hz, 1H), 3.32 (t, 12.0Hz, 1H), 3.69 (t, 10.8 Hz, 1H), 3.86 (dq, 4.5 Hz, 11Hz, 1H), 4.43 (t,10.5 Hz, 1H), 7.13 (dd, 1.9 Hz, 8.8 Hz, 1H), 7.24 (d, 1.9 Hz, 1H) 7.58(d, 8.8 Hz, 1H), 7.66 (d, 8.8 Hz, 2H), 7.93 (d, 8.4 Hz, 1H), 8.13 (s,1H).

EXAMPLE 7 7-chloro2,3,3a,4-tetrahydro-4,4-dimethyl-N-[4-(trifluoromethyl)phenyl]-[1]benzothiopyrano[4,3-c]pyrazole2-carboxamide

Step A: 3-(3-chlorophenylthio)-3-methylbutanoic acid

A mixture of 20.0 g (138 mmol) of 3-chlorothiophenol, 13.85 g (138 mmol)of 3-methyl-2-butanoic acid, and 4.1 ml (3.5 g, 42 mmol) of piperidineunder a nitrogen atmosphere was heated under reflux at 105° C. for 28hrs. The reaction mixture was poured into 200 ml of ether and washedwith 1N HCl (2×80 ml) and then the aqueous layers were extracted with 50ml of ether. The combined organic layers were dried (MgSO₄) andconcentrated under reduced pressure to give 33.1 g of a yellow oil. The1H NMR was consistent with the structure for the title compound.

Step B: 7-chloro-2,3-dihydro-2,2-dimethyl-4H-1-benzothiopyran-4-one

To 270 g of polyphosphoric acid heated to 70° C. was added, portionwise,31.9 g of the product from Step A over 15 min with mechanical stirringunder a nitrogen atmosphere. After heating at 70° C. for an additional45 min, the reaction mixture was cooled to 0° C. and 150 ml of water wascarefully added followed by 100 ml of ether. The resulting mixture wasfurther diluted with 170 ml of water and 110 ml of ether. The layerswere separated and the aqueous layer was extracted with ether (2×200ml). The combined ether layers were washed with 100 ml of 1N NaOH andwere then dried (MgSO₄) and concentrated under reduced pressure to give25.8 g of a yellow solid. The ¹ H NMR was consistent with a 68:32mixture of the structure for Step B and its 5-chloro isomer,respectively.

Step C:7-chloro-3-[(dimethylamino)methyl]-2,3-dihydro-2,2-dimethyl-4H-1-benzothiopyran-4-one

A mixture of 10.0 g (44.1 mmol) of the isomeric thiochromanones fromStep B, 1.99 g (66.2 mmol) of paraformaldehyde 4.32 g (52.9 mmol) ofdimethylamine hydrochloride, and 0.74 ml of concentrated HCl in 15 ml ofethanol under a nitrogen atmosphere was heated under reflux for 49hours. The reaction mixture was poured into 1000 ml of water andextracted with ether (5×200 ml). The aqueous layer was made basic (pH10) with 1N NaOH and then extracted with ethyl acetate (3×200 ml). Afterbeing dried (MgSO₄), these ethyl acetate extracts were concentratedunder reduced pressure to give 3.59 g of an oil. The ¹ H NMR wasconsistent with a 80:20 mixture of the structure for the title compoundof Step C and its 5-chloro isomer, respectively.

Step D:7-chloro-2,3,3a,4-tetrahydro-4,4-dimethyl-N-[4-(trifluoromethyl)phenyl]-[1]benzothiopyrano[4,3-c]pyrazole-2-carboxamide

To a stirred mixture of 3.20 g (111.3 mmol) of the Mannich bases fromStep C and 1.28 ml (1.32 g, 22.6 mmol) of hydrazine hydrate in 7.5 ml ofn-propanol under a nitrogen atmosphere was added 90 mg (1.1 mmol) of 50%aqueous NaOH and the resulting mixture was heated at 100° C. for 2 hrs.The reaction mixture was concentrated under reduced pressure, dilutedwith 50 ml of dichloromethane, and washed with 100 ml of dilute aqueoussodium bicarbonate. The aqueous layer was extracted with 20 ml ofdichloromethane. The combined organic layers were dried (MgSO₄) andfiltered to give 93 ml of solution. A 27 ml portion of this solution wastreated with 0.68 g (3.6 mmol) of 4-(trifluoromethyl)phenyl isocyanateand allowed to stir at room temperature for 2.5 hrs. The reactionmixture was concentrated under reduced pressure, and the residue wastriturated with 15 ml of ether and filtered to give 1.03 g (71%) of thetitle compound as a yellow solid, m.p. 200° C. to 202° C. ¹ H NMR(CDCl₃, 200 MHz) δ 1.35 (s, 3H), 1.45 (s, 3H), 3.83 (m, 2H), 4.21 (m,1H), 7.14 (dd, 2.0 Hz, 8.4 Hz, 1H), 7.22 (d, 1.8 Hz, 1H), 7.58 (d, 8.8Hz, 2H), 7.66 (d, 8.9 Hz, 2H), 7.95 (d, 8.1 Hz, 1H), 8.13 (s, 1H).

EXAMPLE 83a-(4-chlorophenyl)-3,3a,4,5-tetrahydro-N-[4-(trifluoromethyl)phenyl]-2H-benz[q]indazole-2-carboxamide

Step A: 4-chloro-2-(2-phenylethyl)benzeneacetic acid, methyl ester

To a solution of 4.35 g of 60% sodium hydride in 50 ml of DMF was addeddropwise 20.0 g of methyl 4-chlorophenyl acetate in 25 ml of DMF. Oncethe evolution had ceased a mixture of 20.0 g of 2-bromoethyl benzene in25 m of DMF was added and the reaction was stirred at room temPeratureovernight. The reaction was then partitioned between 400 ml of ether and200 ml of H₂ O. The ether extracts were washed with H₂ O, dried overmagnesium sulfate, filtered and concentrated to 32.9 g of a yellow oil.Chromatography on silica gel with 5% ethyl acetate in hexane afforded12.6 g of the title compound as a clear, colorless oil.

Step B: 2-(4-chlorophenyl)-3,4-dihydro-1(2H)naphthalenene

A mixture of 12.6 g of the title compound from Step A, 100 ml ofmethanol, 30 ml of H₂ O and 10 ml of 50% NaOH were refluxed under N₂overnight. The reaction was then concentrated at reduced pressure andconcentrated HCl was added until acidic. The mixture was extracted threetimes with ether, dried over magnesium sulfate and concentrated toafford 12.14 g of a yellow oil. The residue was dissolved in 20 ml ofthionyl chloride and heated at reflux under N₂, overnight. Thionylchloride was removed by concentration at reduced pressure and theresidue was concentrated twice from carbon tetrachloride. The crudeproduct was dissolved in 50 ml of dichloroethane, cooled under N₂ to 0°C. and 5.9 g of aluminum trichloride was added. The reaction was stirredovernight at room temperature, poured into 50 ml of 1N HCl and extractedwith methylene chloride. The organic extracts were dried over magnesiumsulfate, filtered and concentrated to 12.3 g of a brown solid.Chromatography on silica gel with 10% ethyl acetate/hexane followed bytrituration with methanol afforded 5.51 g of the title compound as abrown solid, m.p. 97° to 99° C.

Step C:2-(4-chlorophenyl)-3,4-dihydro-2-(hydroxymethyl)-1(2H)-naphthalenone

To 10 ml of ethanol was added a solution of 1.0 g of the title compoundfrom Step B in 2 ml of toluene followed by 1.5 ml of 37% formaldehydeand then 7.8 ml of 0.5 M NaOH. The reaction was stirred at roomtemperature, under N₂, for four hours after which time TLC confirmeddisappearance of the starting tetralone. The reaction was poured into amixture of 100 ml 5% aqueous sodium bicarbonate and 100 ml of ethylacetate. The aqueous extracts were washed twice with ethyl acetate, theorganic extracts were then dried over magnesium sulfate, filtered andconcentrated at reduced pressure. Chromatography on silica gel with 20%ethyl acetate/hexane afforded 1.19 g of a brown oil. ¹ H NMR wasconsistent with the structure of the title compound.

Step D:2-(4-chlorophenyl)-3,4-dihydro-2-[(methylsulfonyloxy)methyl]-1(2H)-naphthalenone

To a mixture of 0.99 g of the title compound of Step C and 0.6 ml ofmethanesulfonyl chloride in 20 ml of THF at 0° C. was added 1.05 ml oftriethylamine. The reaction was stirred overnight at room temperature,partitioned between 5% aqueous sodium bicarbonate and chloroform, driedover magnesium sulfate and concentrated. The residue was chromatographedon silica gel with 30% ethyl acetate/hexane to afford 1.1 g of the titlecompound as a viscous yellow oil.

Step E:3a-(4-chlorophenyl)-3,3a,4,5-tetrahydro-N-[4-(trifluoromethyl)phenyl]-2H-benz[g]indazole-2-carboxamide

A mixture of 0.9 g of the title compound of Step D, 10 ml of ethanol and0.4 ml of hyrazine hydrate was refluxed under N₂ for 4 days. Thereaction was cooled to room temperature and the white precipitate whichformed was filtered. The filtrate was partitioned between saturatedaqueous potassium bicarbonate and ethyl acetate. The organic extractswere dried over magnesium sulfate, filtered and concentrated at reducedpressure to afford 0.58 g of a gummy yellow solid. The crude residue wasdissolved in 5 ml of THF and 0.4 ml of 4-trifluoromethylphenylisocyanate was added. After 15 minutes TLC on silica gel (30% ethylacetate/hexane) indicated formation of a fluorescent product.Concentration of the reaction mixture under reduced pressure andchromatography on silica gel with 20% ethyl acetate/hexane followed bychromatography on silica gel with 10% methylene chloride inn-butylchloride afforded after trituration with hexane 49.2 mg of abeige powder. ¹ H NMR was consistent with the structure of the titlecompound. ¹ NMR (CDCl₃ ) w 2.30 (dt, 1H), 2.5-2.9 (m, 3H), 3.90 (d, 1H),4.33 (d, 1 H), 7.14 (m, 3H), 7.2-7.4 (m, 3H), 7.56 (d, 2H), 7.65 (d,2H), 8.11 (m, 1 H), 8.28 1H).

By the general Procedures described herein, or obvious modificationsthereof, the compounds of Tables 1 through 18 can be prepared.

    ______________________________________                                        General Structures for Tables 1-18                                            Table       Q                                                                 ______________________________________                                                     ##STR14##                                                        1           Q-1 (J = K = H, R.sub.8 = H)                                      2           Q-2 (J = K = H, R.sub.8 = H)                                      3           Q-3 (J = K = H, R.sub.8 = H)                                      4           Q-4 (J = K = H, X = O, X.sup.1 = O)                               5           Q-5 (J = K = H, X = O, X.sup.1 = O)                                            ##STR15##                                                        6           Q-1 (J = K = H)                                                   7           Q-2 (J = K = H)                                                   8           Q-3 (J = K = H)                                                   9           Q-4 (J = K = H, X.sup.1 = O)                                      10          Q-5 (J = K = H, X.sup. 1 = O))                                                 ##STR16##                                                        11          Q-1                                                               12          Q-2                                                               13          Q-3                                                               14          Q-4 (X.sup.1 = O)                                                 15          Q-5 (X.sup.1 = O)                                                 16                                                                                         ##STR17##                                                        17                                                                                         ##STR18##                                                        18                                                                                         ##STR19##                                                        ______________________________________                                    

For the tables that follow, the values of Q will be numbered as shown:##STR20##

For Tables 16, 17 and 18 only one of the two possible enantiomers of Qis shown for clarity. For compounds in Tables 17 and 18, when V is SO,the a isomer represents compounds where the B substituent is cis to theoxygen of the sulfoxide. The β isomer represents those compounds wherethe B substituent is trans to the oxygen of the sulfoxide.

                                      TABLE 1                                     __________________________________________________________________________                                                Phys.                             R.sub.1.sup.a                                                                            R.sub.1.sup.b                                                                      R.sub.2   B         x   t   Prop. (m.p.                       __________________________________________________________________________                                                °C.)                       H          H    H         H         O   0                                     4-Cl       H    H         H         O   0                                     4-F        H    H         H         O   0                                     4-Br       H    H         H         O   0                                     4-CF.sub.3 H    H         H         O   0                                     4-OCF.sub.2 H                                                                            H    H         H         O   0                                     4-CF.sub.3 3-Cl H         H         O   0                                     4-CO.sub.2 Me                                                                            H    H         H         O   0                                     4-CO.sub.2 -i-Pr                                                                         H    H         H         O   0                                     4-NO.sub.2 H    H         H         O   0                                     4-SMe      H    H         H         O   0                                     4-SO.sub.2 Me                                                                            H    H         H         O   0                                     4-CF.sub.2 Cl                                                                            H    H         H         O   0                                     4-OCF.sub.3                                                                              H    H         H         O   0                                     4-I        H    H         H         O   0                                     4-OCF.sub.2 CF.sub.2 H                                                                   H    H         H         O   0                                     4-CN       H    H         H         O   0                                     4-Me       H    H         H         O   0                                     3,4-CF.sub.2 CF.sub.2 O                                                                       H         H         O   0                                     3,4-OCF.sub.2 CF.sub.2                                                                        H         H         O   0                                     3,4-(Me).sub.2 CCH.sub.2 O                                                                    H         H         O   0                                     4-Cl       H    H         Me        O   0                                     4-Br       H    H         Me        O   0                                     4-CF.sub.3 H    H         Me        O   0                                     4-SMe      H    H         Me        O   0                                     4-OCF.sub.2 H                                                                            H    H         Me        O   0                                     4-CF.sub.2 Cl                                                                            H    H         Me        O   0                                     4-CO.sub.2 i-Pr                                                                          H    H         Me        O   0                                     4-Cl       H    H         allyl     O   0                                     4-Br       H    H         allyl     O   0                                     4-CF.sub.3 H    H         allyl     O   0                                     4-Cl       H    H         CH.sub.2 Ph                                                                             O   0                                     4-Br       H    H         CH.sub.2 Ph                                                                             O   0                                     4-CF.sub.3 H    H         CH.sub.2 Ph                                                                             O   0                                     4-CF.sub.3 3-Cl H         4-FCH.sub.2 Ph                                                                          O   0                                     4-SMe      H    H         4-FCH.sub.2 Ph                                                                          O   0                                     4-Cl       H    H         4-FCH.sub.2 Ph                                                                          O   0                                     4-F        H    H         4-ClCH.sub.2 Ph                                                                         O   0                                     4-NO.sub.2 H    H         4-ClCH.sub.2 Ph                                                                         O   0                                     4-OCF.sub.2 H                                                                            H    H         Ph        O   0                                     4-OCF.sub.3                                                                              H    H         Ph        O   0                                     4-CF.sub.3 H    H         Ph        O   0                                     4-Cl       3-Cl H         4-Cl-Ph   O   0                                     4-Br       H    H         4-Cl-Ph   O   0                                     4-OMe      H    H         4-Cl-Ph   O   0                                     4-CF.sub.3 H    H         n-Bu      O   0                                     4-Cl       H    H         n-Bu      O   0                                     4-CF.sub.3 H    H         (CH.sub.2).sub.3 Cl                                                                     O   0                                     4-Cl       H    H         (CH.sub.2).sub.3 Cl                                                                     O   0                                     4-Br       H    H         CH.sub.2 CF.sub.3                                                                       O   0                                     4-OCF.sub.3                                                                              H    H         CH.sub.2 CF.sub.3                                                                       O   0                                     4-SCF.sub.2 H                                                                            H    H         CH.sub.2 OMe                                                                            O   0                                     4-CF.sub.3 H    H         CH.sub.2 OEt                                                                            O   0                                     4-Cl       H    H         CH.sub.2 CO.sub.2 Me                                                                    O   0                                     4-Br       H    H         CH.sub.2 CO.sub.2 Me                                                                    O   0                                     4-OCF.sub.2 H                                                                            H    H         CH.sub.2 CN                                                                             O   0                                     4-OCF.sub.2 CF.sub.2 H                                                                   H    H         (CH.sub.2).sub.2 CN                                                                     O   0                                     4-CF.sub.3 H    H         CO.sub.2 Me                                                                             O   0                                     4-Cl       H    H         CO.sub.2 Me                                                                             O   0                                     4-Br       H    H         CO.sub.2 Me                                                                             O   0                                     4-F        H    H         CO.sub.2 Me                                                                             O   0                                     4-CF.sub.2 Cl                                                                            H    H         CO.sub.2 Me                                                                             O   0                                     4-OCF.sub.3                                                                              H    H         CO.sub.2 Me                                                                             O   0                                     3,4-CF.sub.2 CF.sub.2 O*                                                                      H         CO.sub.2 Me                                                                             O   0                                     3,4-OCF.sub.2 CF.sub.2                                                                        H         CO.sub.2 Me                                                                             O   0                                     3,4-(Me).sub.2 CCH.sub.2 O                                                                    H         CO.sub.2 Me                                                                             O   0                                     4-CF.sub.3 H    H         CO.sub.2 Et                                                                             O   0                                     4-Br       H    H         CO.sub.2 Et                                                                             O   0                                     4-CF.sub.3 H    H         CO.sub.2 H                                                                              O   0                                     4-Cl       H    H         CO.sub.2 H                                                                              O   0                                     4-CF.sub.3 H    H         CO.sub.2 Ph                                                                             O   0                                     4-F        H    H         CO.sub.2 Ph                                                                             O   0                                     4-CF.sub.3 H    H         CO.sub.2 CH.sub.2 CF.sub.3                                                              O   0                                     4-CF.sub.3 H    H         CO.sub.2 CH.sub.2 CF.sub.3                                                              O   0                                     4-CF.sub.3 H    H         CO.sub.2 CH.sub.2 CN                                                                    O   0                                     4-CF.sub.3 H    H         CO.sub.2 CH.sub.2 CN                                                                    O   0                                     4-CF.sub.3 H    H         CO.sub.2 n-C.sub.6 H.sub.13                                                             O   0                                     4-CF.sub.3 H    H         CO.sub.2 allyl                                                                          O   0                                     4-CF.sub.3 H    H         CO.sub.2 CH.sub.2 Ph                                                                    O   0                                     4-CF.sub.3 H    H         CO.sub.2 CH.sub.2 SMe                                                                   O   0                                     4-CF.sub.3 H    H         C(O)NH.sub.2                                                                            O   0                                     4-Cl       H    H         C(O)NH.sub.2                                                                            O   0                                     4-Br       H    H         C(O)NHMe  O   0                                     4-OCF.sub.3                                                                              H    H         C(O)NHMe  O   0                                     4-CF.sub.3 H    H         C(O)NMe.sub.2                                                                           O   0                                     4-Cl       H    H         C(O)NMe.sub.2                                                                           O   0                                     4-Br       H    H         C(O)NHEt  O   0                                     4-OCF.sub.3                                                                              H    H         C(S)NH.sub.2                                                                            O   0                                     4-CF.sub.3 H    H         C(S)NHMe  O   0                                     4-Cl       H    H         C(S)NMe.sub.2                                                                           O   0                                     4-Br       H    H         C(S)Me    O   0                                     4-OCF.sub.3                                                                              H    H         C(S)Et    O   0                                     4-CF.sub.3 H    H         C(S)NMe.sub.2                                                                           O   0                                     4-Cl       H    H         C(S)NHMe  O   0                                     4-OCF.sub.3                                                                              H    H         OH        O   0                                     4-CF.sub.3 H    H         OH        O   0                                     4-Cl       H    H         OH        O   0                                     4-Br       H    H         OH        O   0                                     4-OCF.sub.2 H                                                                            H    OH        O         0                                         4-CF.sub.3 H    H         OMe       O   0                                     4-CF.sub.3 H    H         OMe       O   0                                     4-Cl       H    H         OMe       O   0                                     4-Br       H    H         O-allyl   O   0                                     4-OCF.sub.2 H                                                                            H    H         O-allyl   O   0                                     4-OCF.sub.3                                                                              H    H         O-allyl   O   0                                     4-CF.sub.3 H    H         OAc       O   0                                     4-Cl       H    H         OAc       O   0                                     4-Br       H    H         OCONHMe   O   0                                     4-OCF.sub.2 H                                                                            H    H         OCONMe.sub.2                                                                            O   0                                     4-OCF.sub.3                                                                              H    H         OCO.sub.2 Me                                                                            O   0                                     4-CF.sub.3 H    H         OCO.sub.2 Ph                                                                            O   0                                     4-Cl       H    H         OSO.sub.2 Me                                                                            O   0                                     4-Br       H    H         OSO.sub.2 Me                                                                            O   0                                     4-OCF.sub.2 H                                                                            H    H         OCH.sub.2 Ph                                                                            O   0                                     4-OCF.sub.3                                                                              H    H         OCH.sub.2 Ph                                                                            O   0                                     H          H    H         H         O   1                                     4-Cl       H    H         H         O   1   91.5 to 96                        4-F        H    H         H         O   1                                     4-Br       H    H         H         O   1   151 to 152                        4-CF.sub.3 H    H         H         O   1   149 to 151                        4-OCF.sub.2 H                                                                            H    H         H         O   1                                     4-CF.sub.3 3-Cl H         H         O   1                                     4-CO.sub.2 Me                                                                            H    H         H         O   1                                     4-CO.sub.2 -i-Pr                                                                         H    H         H         O   1                                     4-NO.sub.2 H    H         H         O   1                                     4-SMe      H    H         H         O   1                                     4-SO.sub.2 Me                                                                            H    H         H         O   1                                     4-CF.sub.2 Cl                                                                            H    H         H         O   1                                     4-OCF.sub.3                                                                              H    H         H         O   1   104 to 107                        4-I        H    H         H         O   1                                     4-OCF.sub.2 CF.sub.2 H                                                                   H    H         H         O   1                                     4-CN       H    H         H         O   1                                     4-Me       H    H         H         O   1                                     3,4-CF.sub.2 CF.sub.2 O                                                                       H         H         O   1                                     3,4-OCF.sub.2 CF                                                                              H         H         O   1                                     3,4-(Me).sub.2 CCH.sub.2 O                                                                    H         H         O   1                                     4-Cl       H    H         Me        O   1                                     4-Br       H    H         Me        O   1                                     4-CF.sub.3 H    H         Me        O   1   151.5 to 153.5                    4-SMe      H    H         Me        O   1                                     4-OCF.sub.2 H                                                                            H    H         Me        O   1                                     4-CF.sub.3 H    H         Et        O   1   120 to 123                        4-CO.sub.2 i-Pr                                                                          H    H         Me        O   1                                     4-Cl       H    H         allyl     O   1                                     4-Br       H    H         allyl     O   1                                     4-CF.sub.3 H    H         allyl     O   1   158 to 163                        4-Cl       H    H         CH.sub.2 Ph                                                                             O   1                                     4-Br       H    H         CH.sub.2 Ph                                                                             O   1                                     4-CF.sub.3 H    H         CH.sub.2 Ph                                                                             O   1   51 to 55                          4-CF.sub.3 3-Cl H         4-FCH.sub.2 Ph                                                                          O   1                                     4-SMe      H    H         4-FCH.sub.2 Ph                                                                          O   1                                     4-CF.sub.3 H    H         4-FCH.sub.2 Ph                                                                          O   1                                     4-CF.sub.3 H    H         4-ClCH.sub.2 Ph                                                                         O   1   gum                               4-NO.sub.2 H    H         4-ClCH.sub.2 Ph                                                                         O   1                                     4-OCF.sub.2 H                                                                            H    H         Ph        O   1                                     4-OCF.sub.3                                                                              H    H         Ph        O   1                                     4-CF.sub.3 H    H         Ph        O   1                                     4-Cl       3-Cl H         4-Cl-Ph   O   1                                     4-Br       H    H         4-Cl-Ph   O   1                                     4-OMe      H    H         4-Cl-Ph   O   1                                     4-CF.sub.3 H    H         n-Bu      O   1                                     4-Cl       H    H         n-Bu      O   1                                     4-CF.sub.3 H    H         (CH.sub.2).sub.3 Cl                                                                     O   1                                     4-Cl       H    H         (CH.sub.2).sub.3 Cl                                                                     O   1                                     4-Br       H    H         CH.sub.2 CF.sub.3                                                                       O   1                                     4-OCF.sub.3                                                                              H    H         CH.sub.2 CF.sub.3                                                                       O   1                                     4-SCF.sub.2 H                                                                            H    H         CH.sub.2 OMe                                                                            O   1                                     4-CF.sub.3 H    H         CH.sub.2 OEt                                                                            O   1                                     4-Cl       H    H         CH.sub.2 CO.sub.2 Me                                                                    O   1                                     4-Br       H    H         CH.sub.2 CO.sub.2 Me                                                                    O   1                                     4-OCF.sub.2 H                                                                            H    H         CH.sub.2 CN                                                                             O   1                                     4-OCF.sub.2 CF.sub.2 H                                                                   H    H         (CH.sub.2).sub.2 CN                                                                     O   1                                     4-CF.sub.3 H    H         (CH.sub.2).sub.2 CN                                                                     O   1   165 to 169                        4-CF.sub.3 H    H         (CH.sub.2).sub.3 CN                                                                     O   1   186 to 188                        4-CF.sub.3 H    H         CO.sub.2 Me                                                                             O   1   177 to 180                        4-Cl       H    H         CO.sub.2 Me                                                                             O   1   175 to 177                        4-Br       H    H         CO.sub.2 Me                                                                             O   1   175 to 178                        4-F        H    H         CO.sub.2 Me                                                                             O   1                                     4-CF.sub.2 Cl                                                                            H    H         CO.sub.2 Me                                                                             O   1                                     4-OCF.sub.3                                                                              H    H         CO.sub.2 Me                                                                             O   1                                     3,4-CF.sub.2 CF.sub.2 O                                                                       H         CO.sub.2 Me                                                                             O   1                                     3,4-OCF.sub.2 CF.sub.2 O                                                                      H         CO.sub.2 Me                                                                             O   1                                     3,4-(Me).sub.2 CCH.sub.2 O                                                                    H         CO.sub.2 Me                                                                             O   1                                     4-CF.sub.3 H    H         CO.sub.2 Et                                                                             O   1   220 to 222                        4-Br       H    H         CO.sub.2 Et                                                                             O   1   179 to 182                        4-Cl       H    H         CO.sub.2 Et                                                                             O   1   172 to 174                        4-CF.sub.3 H    H         CO.sub.2 H                                                                              O   1   182 to 183                        4-CF.sub.3 H    H         CO.sub.2 Na                                                                             O   1   230                               4-CF.sub.3 H    H         CO.sub.2 Ph                                                                             O   1                                     4-F        H    H         CO.sub.2 Ph                                                                             O   1                                     4-CF.sub.3 H    H         CO.sub.2 CH.sub.2 CCL.sub.3                                                             O   1   194 to 196                        4-CF.sub.3 H    H         CO.sub.2 CH.sub.2 CF.sub.3                                                              O   1                                     4-CF.sub.3 H    H         CO.sub.2 (CH.sub.2)CL                                                                   O   1   185 to 188                        4-CF.sub.3 H    H         CO.sub.2 (CH.sub.2).sub.2 Br                                                            O   1   162 to 167                        4-CF.sub.3 H    H         CO.sub.2 CH.sub.2 CN                                                                    O   1                                     4-CF.sub.3 H    H         CO.sub.2 n-C.sub.6 H.sub.13                                                             O   1                                     4-CF.sub.3 H    H         CO.sub.2 allyl                                                                          O   1                                     4-CF.sub.3 H    H         CO.sub.2 CH.sub.2 Ph                                                                    O   1                                     4-CF.sub.3 H    H         CO.sub.2 CH.sub.2 SMe                                                                   O   1                                     4-CF.sub.3 H    H         C(O)NH.sub.2                                                                            O   1   250                               4-Cl       H    H         C(O)NH.sub.2                                                                            O   1                                     4-Br       H    H         C(O)NHMe  O   1                                     4-OCF.sub.3                                                                              H    H         C(O)NHMe  O   1                                     4-CF.sub.3 H    H         C(O)NMe.sub.2                                                                           O   1   226 to 230                        4-Cl       H    H         C(O)NMe.sub.2                                                                           O   1                                     4-Br       H    H         C(O)NHEt  O   1                                     4-CF.sub.3 H    H         C(O)NHMe  O   1   220                               4-CF.sub.3 H    H         C(O)NHallyl                                                                             O   1   250                               4-CF.sub.3 H    H         C(O)N(Me)allyl                                                                          O   1   219 to 221                        4-CF.sub.3 H    H         C(O)NHPh-4-Cl                                                                           O   1   255                               4-CF.sub.3 H    H         C(O)-piperidinyl                                                                        o   1   235                               4-OCF.sub.3                                                                              H    H         C(S)NH.sub.2                                                                            O   1                                     4-CF.sub.3 H    H         C(S)NHMe  O   1                                     4-Cl       H    H         C(S)NMe.sub.2                                                                           O   1                                     4-Br       H    H         C(S)Me    O   1                                     4-OCF.sub.3                                                                              H    H         C(S)Et    O   1                                     4-CF.sub.3 H    H         C(S)NMe.sub.2                                                                           O   1                                     4-Cl       H    H         C(S)NHMe  O   1                                     4-OCF.sub.3                                                                              H    H         OH        O   1                                     4-CF.sub.3 H    H         OH        O   1                                     4-Cl       H    H         OH        O   1                                     4-Br       H    H         OH        O   1                                     4-OCF.sub.2 H                                                                            H    H         OH        O   1                                     4-OCF.sub.3                                                                              H    H         OMe       O   1                                     4-CF.sub.3 H    H         OMe       O   1                                     4-Cl       H    H         OMe       O   1                                     4-Br       H    H         O-allyl   O   1                                     4-OCF.sub.2 H                                                                            H    H         O-allyl   O   1                                     4-OCF.sub.3                                                                              H    H         O-allyl   O   1                                     4-CF.sub.3 H    H         OAc       O   1                                     4-Cl       H    H         OAc       O   1                                     4-OCF.sub.3                                                                              H    H         OCO.sub.2 Me                                                                            O   1                                     4-CF.sub. 3                                                                              H    H         OCO.sub.2 Me                                                                            O   1                                     4-Cl       H    H         OSO.sub.2 Me                                                                            O   1                                     4-Br       H    H         OSO.sub.2 Me                                                                            O   1                                     4-OCF.sub.2 H                                                                            H    H         OEt       O   1                                     4-OCF.sub.3                                                                              H    H         OEt       O   1                                     H          H    H         H         O   2                                     4-Cl       H    H         H         O   2   136.5 to 138                      4-F        H    H         H         O   2                                     4-Br       H    H         H         O   2                                     4-CF.sub.3 H    H         H         O   2    167 to 168.5                     4-OCF.sub.2 H                                                                            H    H         H         O   2                                     4-CF.sub.3 3-Cl H         H         O   2                                     4-CO.sub.2 Me                                                                            H    H         H         O   2                                     4-CO.sub.2 -i-Pr                                                                         H    H         H         O   2                                     4-NO.sub.2 H    H         H         O   2                                     4-SMe      H    H         H         O   2                                     4-SO.sub.2 Me                                                                            H    H         H         O   2                                     4-CF.sub.2 Cl                                                                            H    H         H         O   2                                     4-OCF.sub.3                                                                              H    H         H         O   2                                     4-I        H    H         H         O   2                                     4-OCF.sub.2 CF.sub.2 H                                                                   H    H         H         O   2                                     4-CN       H    H         H         O   2                                     4-Me       H    H         H         O   2                                     4-Cl       H    H         Me        O   2    137 to 141.5                     4-Br       H    H         Me        O   2                                     4-CF.sub.3 H    H         Me        O   2   134 to 139                        4-SMe      H    H         Me        O   2                                     4-OCF.sub.2 H                                                                            H    H         Me        O   2                                     4-CF.sub.2 Cl                                                                            H    H         Me        O   2                                     4-CO.sub.2 i-Pr                                                                          H    H         Me        O   2                                     4-Cl       H    H         allyl     O   2                                     4-Br       H    H         allyl     O   2                                     4-CF.sub.3 H    H         allyl     O   2                                     4-Cl       H    H         CH.sub.2 Ph                                                                             O   2                                     4-Br       H    H         CH.sub.2 Ph                                                                             O   2                                     4-CF.sub.3 H    H         CH.sub.2 Ph                                                                             O   2                                     4-CF.sub.3 3-Cl H         4-FCH.sub.2 Ph                                                                          O   2                                     4-SMe      H    H         4-FCH.sub.2 Ph                                                                          O   2                                     4-Cl       H    H         4-FCH.sub.2 Ph                                                                          O   2                                     4-F        H    H         4-ClCH.sub.2 Ph                                                                         O   2                                     4-NO.sub.2 H    H         4-ClCH.sub.2 Ph                                                                         O   2                                     4-OCF.sub.2 H                                                                            H    H         Ph        O   2                                     4-OCF.sub.3                                                                              H    H         Ph        O   2                                     4-CF.sub.3 H    H         Ph        O   2                                     4-Cl       3-Cl H         4-Cl-Ph   O   2                                     4-Br       H    H         4-Cl-Ph   O   2                                     4-OMe      H    H         4-Cl-Ph   O   2                                     4-CF.sub.3 H    H         n-Bu      O   2                                     4-Cl       H    H         n-Bu      O   2                                     4-CF.sub.3 H    H         (CH.sub.2).sub.3 Cl                                                                     O   2                                     4-Cl       H    H         (CH.sub.2).sub.3 Cl                                                                     O   2                                     4-Br       H    H         CH.sub.2 CF.sub. 3                                                                      O   2                                     4-OCF.sub.3                                                                              H    H         CH.sub.2 CF.sub.3                                                                       O   2                                     4-SCF.sub.2 H                                                                            H    H         CH.sub.2 OMe                                                                            O   2                                     4-CF.sub.3 H    H         CH.sub.2 OEt                                                                            O   2                                     4-Cl       H    H         CH.sub.2 CO.sub.2 Me                                                                    O   2                                     4-Br       H    H         CH.sub.2 CO.sub.2 Me                                                                    O   2                                     4-OCF.sub.2 H                                                                            H    H         CH.sub.2 CN                                                                             O   2                                     4-OCF.sub.2 CF.sub.2 H                                                                   H    H         (CH.sub.2).sub.2 CN                                                                     O   2                                     4-CF.sub.3 H    H         CO.sub.2 Me                                                                             O   2                                     4-Cl       H    H         CO.sub.2 Me                                                                             O   2                                     4-Br       H    H         CO.sub.2 Me                                                                             O   2                                     4-F        H    H         CO.sub.2 Me                                                                             O   2                                     4-CF.sub.2 Cl                                                                            H    H         CO.sub.2 Me                                                                             O   2                                     4-OCF.sub.3                                                                              H    H         CO.sub.2 Me                                                                             O   2                                     4-CF.sub.3 H    H         CO.sub.2 Et                                                                             O   2                                     4-Br       H    H         CO.sub.2 Et                                                                             O   2                                     4-CF.sub.3 H    H         CO.sub.2 H                                                                              O   2                                     4-Cl       H    H         CO.sub.2 H                                                                              O   2                                     4-CF.sub.3 H    H         CO.sub.2 Ph                                                                             O   2                                     4-F        H    H         CO.sub.2 Ph                                                                             O   2                                     4-CF.sub.3 H    H         CO.sub.2 CH.sub.2 CF.sub.3                                                              O   2                                     4-CF.sub.3 H    H         CO.sub.2 CH.sub.2 CF.sub. 3                                                             O   2                                     4-CF.sub.3 H    H         CO.sub.2 CH.sub.2 CN                                                                    O   2                                     4-CF.sub.3 H    H         CO.sub.2 CH.sub.2 CN                                                                    O   2                                     4-CF.sub.3 H    H         CO.sub.2 n-C.sub.6 H.sub.13                                                             O   2                                     4-CF.sub.3 H    H         CO.sub.2 allyl                                                                          O   2                                     4-CF.sub.3 H    H         CO.sub.2 CH.sub.2 Ph                                                                    O   2                                     4-CF.sub.3 H    H         CO.sub.2 CH.sub.2 SMe                                                                   O   2                                     4-CF.sub.3 H    H         C(O)NH.sub.2                                                                            O   2                                     4-Cl       H    H         C(O)NH.sub.2                                                                            O   2                                     4-Br       H    H         C(O)NHMe  O   2                                     4-OCF.sub.3                                                                              H    H         C(O)NHMe  O   2                                     4-CF.sub.3 H    H         C(O)NMe.sub.2                                                                           O   2                                     4-Cl       H    H         C(O)NMe.sub.2                                                                           O   2                                     4-Br       H    H         C(O)NHEt  O   2                                     4-OCF.sub.3                                                                              H    H         C(S)NH.sub.2                                                                            O   2                                     4-CF.sub.3 H    H         C(S)NHMe  O   2                                     4-Cl       H    H         C(S)NMe.sub.2                                                                           O   2                                     4-Br       H    H         C(S)Me    O   2                                     4-OCF.sub.3                                                                              H    H         C(S)Et    O   2                                     4-CF.sub.3 H    H         C(S)NMe.sub.2                                                                           O   2                                     4-Cl       H    H         C(S)NHMe  O   2                                     4-OCF.sub.3                                                                              H    H         OH        O   2                                     4-CF.sub.3 H    H         OH        O   2                                     4-Cl       H    H         OH        O   2                                     4-Br       H    H         OH        O   2                                     4-OCF.sub.2 H                                                                            H    H         OH        O   2                                     4-OCF.sub.3                                                                              H    H         OMe       O   2                                     4-CF.sub.3 H    H         OMe       O   2                                     4-Cl       H    H         OMe       O   2                                     4-Br       H    H         O-allyl   O   2                                     4-OCF.sub.2 H                                                                            H    H         O-allyl   O   2                                     4-OCF.sub.3                                                                              H    H         O-allyl   O   2                                     4-CF.sub.3 H    H         OAc       O   2                                     4-Cl       H    H         OAc       O   2                                     4-Br       H    H         OCONHMe   O   2                                     4-OCF.sub.2 H                                                                            H    H         OCONMe.sub.2                                                                            O   2                                     4-OCF.sub.3                                                                              H    H         OCO.sub.2 Me                                                                            O   2                                     4-CF.sub.3 H    H         OCO.sub.2 Me                                                                            O   2                                     4-Cl       H    H         OSO.sub.2 Me                                                                            O   2                                     4-Br       H    H         OSO.sub.2 Me                                                                            O   2                                     4-OCF.sub.2 H                                                                            H    H         OCH.sub.2 Ph                                                                            O   2                                     4-OCF.sub.3                                                                              H    H         OCH.sub.2 Ph                                                                            O   2                                     4-CF.sub.3 H    5-Cl      H         O   0                                     4-OCF.sub.3                                                                              H    4-Cl      Me        O   0                                     4-OCF.sub.2 H                                                                            H    5-Cl      CO.sub.2 Me                                                                             O   0                                     4-Cl       H    5-Cl      CO.sub.2 CH.sub.2 CH.sub.2 Cl                                                           O   0                                     4-Br       H    5-Cl      H         O   1   164 to 166                        4-CF.sub.3 H    5-Cl      Me        O   1                                     4-OCF.sub.3                                                                              H    5-Cl      Et        O   1                                     4-Cl       H    5-Cl      H         O   1   155 to 157                        4-SMe      H    5-Cl      H         O   1   159 to 161                        4-CO.sub. 2 Et                                                                           H    5-Cl      H         O   1   153 to 156                        4-Br       H    5-Cl      CO.sub.2 Me                                                                             O   1   234 to 236                        4-SMe      H    5-Cl      CO.sub.2 Me                                                                             O   1   202 to 204                        4-CO.sub.2 Et                                                                            H    5-Cl      CO.sub.2 Me                                                                             O   1   197 to 199                        4-OCF.sub.2 H                                                                            H    5-Cl      CO.sub.2 Me                                                                             O   1                                     4-Cl       H    5-Cl      CO.sub.2 Me                                                                             O   1   222 to 233                        4-Br       H    5-Cl      C(O)Me    O   1                                     4-CF.sub.3 H    5-Cl      C(O)Et    O   1                                     4-OCF.sub.3                                                                              H    5-Cl      C(O)NMe.sub.2                                                                           O   1                                     4-OCF.sub.2 H                                                                            H    5-Cl      OH        O   1                                     4-Cl       H    5-Cl      OAc       O   1                                     4-Br       H    5-Cl      H         O   2                                     4-CF.sub.3 H    5-Cl      Me        O   2                                     4-OCF.sub.3                                                                              H    5-Cl      CO.sub.2 Me                                                                             O   2                                     4-OCF.sub.2 H                                                                            H    5-Cl      CO.sub.2 -n-Bu                                                                          O   2                                     4-Cl       H    5-Cl      CH.sub.2 Ph                                                                             O   2                                     4-Br       H    5-Cl      C(O)NHPh  O   2                                     4-CF.sub.3 H    5-Cl      OMe       O   2                                     4-OCF.sub.3                                                                              H    5-Cl      OC(O)NHMe O   2                                     4-CF.sub.3 H    5-F       CO.sub.2 Me                                                                             O   0                                     4-OCF.sub.3                                                                              H    5-F       CO.sub.2 Me                                                                             O   0                                     4-OCF.sub.2 H                                                                            H    5-F       CO.sub.2 Me                                                                             O   0                                     4-CF.sub.3 H    5-F       H         O   1   175 to 178                        4-Cl       H    5-F       H         O   1                                     4-Br       H    5-F       H         O   1                                     4-OCF.sub.2 H                                                                            H    5-F       H         O   1                                     4-Cl       H    5-F       CO.sub.2 Me                                                                             O   1                                     4-Br       H    5-F       CO.sub.2 Me                                                                             O   1                                     4-CF.sub.3 H    5-F       CO.sub.2 Me                                                                             O   1   223 to 225                        4-OCF.sub.3                                                                              H    5-F       CO.sub.2 Me                                                                             O   2                                     4-OCF.sub.2 H                                                                            H    5-F       CO.sub.2 Me                                                                             O   2                                     4-Cl       H    5-F       CO.sub.2 Me                                                                             O   2                                     4-Br       H    5-OCF.sub.2 H                                                                           CO.sub.2 Me                                                                             O   0                                     4-CF.sub.3 H    5-OCF.sub.2 H                                                                           CO.sub.2 Me                                                                             O   0                                     4-OCF.sub.3                                                                              H    5-OCF.sub.2 H                                                                           CO.sub.2 Me                                                                             O   0                                     4-OCF.sub.2 H                                                                            H    5-OCF.sub.2 H                                                                           CO.sub.2 Me                                                                             O   1                                     4-Cl       H    5-OCF.sub.2 H                                                                           CO.sub.2 Me                                                                             O   1                                     4-Br       H    5-OCF.sub.2 H                                                                           CO.sub.2 Me                                                                             O   1                                     4-CF.sub.3 H    5-OCF.sub.2 H                                                                           CO.sub.2 Me                                                                             O   2                                     4-OCF.sub.3                                                                              H    5-OCF.sub.2 H                                                                           CO.sub.2 Me                                                                             O   2                                     4-OCF.sub.2 H                                                                            H    5-OCF.sub.2 H                                                                           CO.sub.2 Me                                                                             O   2                                     4-Cl       H    5-Br      CO.sub.2 Me                                                                             O   1                                     4-Br       H    5-NO.sub.2                                                                              CO.sub.2 Me                                                                             O   1                                     4-CF.sub.3 H    5-CF.sub.3                                                                              CO.sub.2 Me                                                                             O   1                                     4-OCF.sub.3                                                                              H    5-OCH.sub.3                                                                             CO.sub.2 Me                                                                             O   1                                     4-CF.sub.3 H    5-OCH.sub.2 Ph                                                                          Me        O   1                                     4-CF.sub.3 H    5-C(O)Me  Et        O   1                                     4-CF.sub.3 H    5-OCF.sub.2 CF.sub.2 H                                                                  CO.sub.2 Me                                                                             O   1                                     4-CF.sub.3 H    5-I       Me        O   1                                     4-CF.sub.3 H    5-OCF.sub.3                                                                             Et        O   1                                     4-CF.sub.3 H    5-Et      C(O)Me    O   1                                     4-CF.sub.3 H    5-Me      C(O)CF.sub.3                                                                            O   1                                     4-CF.sub.3 H    5-CN      Me        O   1                                     4-CF.sub.3 H    5-OMe     CO.sub.2 Me                                                                             O   1   180 to 186                        4-CF.sub.3 H    5-OMe     CO.sub.2 Et                                                                             O   1   160 to 166                        4-CF.sub.3 H    5-OMe     H         O   1   158 to 160                        4-Cl       H    5-OMe     H         O   1   169 to 171                        4-CF.sub.3 H    5-CO.sub.2 Me                                                                           n-C.sub.6 H.sub.13                                                                      O   1                                     4-CF.sub.3 H    5-SCF.sub.2 H                                                                           C(O)H     O   1                                     4-CF.sub.3 H    5-SO.sub.2 Me                                                                           (CH.sub.2).sub.4 Cl                                                                     O   1                                     4-CF.sub.3 H    5,6-di-Cl H         O   1   229 to 230                        4-CF.sub.3 H    5,6-di-Cl CO.sub.2 Me                                                                             O   1   238 to 241                        4-CF.sub.3 H    4-F       H         O   1   183 to 184                        4-Cl       H    4-F       CO.sub.2 Me                                                                             O   1                                     4-Br       H    4-F       CO.sub.2 Me                                                                             O   1                                     4-CF.sub. 3                                                                              H    4-Cl      H         O   1   179 to 180                        4-OCF.sub.2 H                                                                            H    4-Cl      H         O   1                                     4-OCF.sub.2 H                                                                            H    4-Cl      CO.sub.2 Me                                                                             O   1                                     4-CF.sub.3 H    4-Br      H         O   1                                     4-CF.sub.3 H    4-Br      CO.sub.2 Me                                                                             O   1                                     4-CF.sub.3 H    6-Cl      CO.sub.2 Me                                                                             O   1                                     4-CF.sub.3 H    6-F       CO.sub.2 Me                                                                             O   1                                     4-CF.sub.3 H    6-CF.sub.3                                                                              CO.sub.2 Me                                                                             O   1                                     4-CF.sub.3 H    4-Cl      CO.sub.2 Me                                                                             O   1                                     4-CF.sub.3 H    4-F       CO.sub.2 Me                                                                             O   1   206 to 212                        4-CF.sub.3 H    6-Br      CO.sub.2 Me                                                                             O   1                                     4-CF.sub.3 H    6-NO.sub.2                                                                              CO.sub.2 Me                                                                             O   1                                     4-CF.sub.3 H    6-Me      CO.sub.2 Me                                                                             O   1                                     4-CF.sub.3 H    4-Cl      CO.sub.2 Me                                                                             O   1   209 to 211                        4-CF.sub.3 H    4-F       CO.sub.2 Me                                                                             O   1                                     4-CF.sub.3 H    4-Br      CO.sub.2 Me                                                                             O   1                                     4-CF.sub.3 H    H         H         S   0                                     4-Cl       H    H         Me        S   0                                     4-CF.sub.3 H    H         CO.sub.2 Me                                                                             S   0                                     4-Cl       H    H         H         S   1                                     4-CF.sub.3 H    H         Me        S   1                                     4-Cl       H    H         CO.sub.2 Me                                                                             S   1                                     4-CF.sub.3 H    H         H         S   2                                     4-Cl       H    H         Me        S   2                                     4-CF.sub.3 H    H         CO.sub.2 Me                                                                             S   2                                     4-Cl       H    5-Cl      H         S   1                                     4-CF.sub.3 H    5-Cl      Me        S   1                                     4-Cl       H    5-Cl      CO.sub.2 Me                                                                             S   1                                     4-CF.sub.3 H    5-F       H         S   1                                     4-Cl       H    5-F       Me        S   1                                     4-CF.sub.3 H    5-F       CO.sub.2 Me                                                                             S   1                                     __________________________________________________________________________      *as a representative example this substitution pattern designates            ##STR21##                                                                

                                      TABLE 2                                     __________________________________________________________________________                                   Phys.                                          R.sub.1.sup.a                                                                      R.sub.1.sup.b                                                                    R.sub.2                                                                            B       x t v     Prop. (m.p. °C.)                        __________________________________________________________________________    4-CF.sub.3                                                                         H  H    H       O 0 O                                                    4-CF.sub.2 Cl                                                                      3-Cl                                                                             H    H       O 1 O                                                    4-CF.sub.3                                                                         H  H    H       O 1 O     161 to 164                                     4-Cl 3-Cl                                                                             H    H       O 1 O     220 to 224                                     4-Br H  H    H       O 1 O     215 to 220                                     3-CF.sub.3                                                                         H  H    H       O 1 O     165 to 167                                     4-Cl H  H    H       O 1 O     192 to 199                                     3-Cl H  H    H       O 1 O     162 to 171                                     4-CF.sub.3                                                                         H  5-Br H       O 1 O     192 to 195                                     4-Cl H  5-Br H       O 1 O     144 to 150                                     4-Br H  5-Br H       O 1 O     218 to 221                                     4-Cl H  7-Br H       O 1 O     180 to 184                                     4-CF.sub.3                                                                         H  7-Br H       O 1 O     161 to 182                                     4-Br H  7-Br H       O 1 O     179 to 202                                     4-CF.sub.3                                                                         H  5-Cl H       O 1 O     152 to 182                                     4-Cl H  5-Cl H       O 1 O     193 to 207                                     4-Cl H  5-F  H       O 1 O                                                    4-CO.sub.2 Me                                                                      H  5-F  H       O 2 O                                                    4-Br H  5-Cl H       O 1 O     228 to 232                                     4-CF.sub.3                                                                         H  7-Cl H       O 1 O     178 to 202                                     4-Cl H  7-Cl H       O 1 O     179 to 193                                     4-Br H  7-Cl H       O 1 O     201 to 208                                     4-CF.sub.3                                                                         H  H    Me      O 1 O                                                    4-CF.sub.2 Cl                                                                      3-Cl                                                                             5-Cl Me      O 2 O                                                    4-OCF.sub.3                                                                        H  5-Cl Me      O 0 O                                                    4-OCF.sub.2 H                                                                      H  5-F  Me      O 1 O                                                    4-Cl H  5-F  Me      O 2 O                                                    4-CO.sub.2 Me                                                                      H  H    Me      O 0 O                                                    4-Br H  H    Me      O 1 O                                                    4-CF.sub.3                                                                         H  5-Cl CO.sub.2 Me                                                                           O 2 O                                                    4-CF.sub.2 Cl                                                                      3-Cl                                                                             5-Cl CO.sub.2 Me                                                                           O 0 O                                                    4-OCF.sub.3                                                                        H  H    CO.sub.2 Me                                                                           O 1 O                                                    4-OCF.sub.2 H                                                                      H  H    CO.sub.2 Me                                                                           O 2 O                                                    4-Cl H  5-Cl CO.sub.2 Me                                                                           O 0 O                                                    4-CO.sub.2 Me                                                                      H  5-Cl CO.sub.2 Me                                                                           O 1 O                                                    4-Br H  5-F  CO.sub.2 Me                                                                           O 2 O                                                    4-CF.sub.3                                                                         H  H    CO.sub.2 Et                                                                           O 0 O                                                    4-Cl H  H    CO.sub.2 CH.sub.2 CF.sub.3                                                            O 1 O                                                    4-CF.sub.3                                                                         H  5-Cl CH.sub.2 CF.sub.3                                                                     O 2 O                                                    4-Cl H  5-Cl C(O)Me  O 0 O                                                    4-CF.sub.3                                                                         H  5-OCF.sub.2 H                                                                      Me      O 1 O                                                    4-CF.sub.3                                                                         H  5-OCF.sub.2 H                                                                      CO.sub.2 Me                                                                           O 2 O                                                    4-Cl H  5-F  CONHMe  O 0 O                                                    4-CF.sub.3                                                                         H  5-F  CONHPh  O 1 O                                                    4-Cl H  H    allyl   O 2 O                                                    4-CF.sub.3                                                                         H  H    CH.sub.2 Ph                                                                           O 0 O                                                    4-Cl H  5-Cl n-Pr    O 1 O                                                    4-CF.sub.3                                                                         H  5-Cl C(O)(CH.sub.2).sub.3 Cl                                                               O 2 O                                                    4-Cl H  5-OCF.sub.2 H                                                                      Me      O 0 O                                                    4-CF.sub.3                                                                         H  5-OCF.sub.2 H                                                                      CO.sub.2 Me                                                                           O 1 O                                                    4-Cl H  5-F  CH.sub.2 CO.sub.2 Me                                                                  O 2 O                                                    4-CF.sub.3                                                                         H  5-F  CO.sub.2 H                                                                            O 0 O                                                    4-Cl H  H    4-Cl-Ph O 1 O                                                    4-CF.sub.3                                                                         H  H    4-Cl-Ph O 2 O                                                    4-Cl H  5-Cl CO.sub.2 Me                                                                           S 0 O                                                    4-CF.sub.3                                                                         H  5-Cl CO.sub.2 Me                                                                           S 1 O                                                    4-Cl H  5-OCF.sub.2 H                                                                      CO.sub.2 Me                                                                           S 2 O                                                    4-CF.sub.3                                                                         H  H    H       O 0 S                                                    4-CF.sub.2 Cl                                                                      3-Cl                                                                             H    H       O 1 S                                                    4-OCF.sub.3                                                                        H  5-Cl H       O 2 S                                                    4-OCF.sub.2 H                                                                      H  5-Cl H       O 0 S                                                    4-Cl H  5-F  H       O 1 S                                                    4-CO.sub.2 Me                                                                      H  5-F  H       O 2 S                                                    4-Br H  H    H       O 0 S                                                    4-CF.sub.3                                                                         H  H    H       O 1 S     170 to 171                                     4-Cl 3-Cl                                                                             H    H       O 1 S     235 to 239                                     4-Br H  H    H       O 1 S     189 to 192                                     3-CF.sub.3                                                                         H  H    H       O 1 S     203 to 204                                     4-Cl H  H    H       O 1 S     178 to 180                                     3-CF.sub.3                                                                         H  5-Cl H       O 1 S     197 to 200                                     4-Cl H  5-Cl H       O 1 S     202 to 206                                     3-Cl H  5-Cl H       O 1 S     224 to 227                                     4-Br H  5-Cl H       O 1 S     207 to 211                                     4-Cl 3-Cl                                                                             5-Cl H       O 1 S     220 to 232                                     4-CF.sub.3                                                                         H  6-Cl H       O 1 S     195 to 202                                     3-CF.sub.3                                                                         H  6-Cl H       O 1 S     207 to 213                                     4-Cl H  6-Cl H       O 1 S     180 to 188                                     3-Cl H  6-Cl H       O 1 S     230 to 240                                     4-Br H  6-Cl H       O 1 S     184 to 189                                     4-Cl 3-Cl                                                                             6-Cl H       O 1 S     227 to 237                                     4-CF.sub.3                                                                         H  5-Br H       O 1 S     212 to 215                                     3-CF.sub.3                                                                         H  5-Br H       O 1 S     187 to 200                                     4-Cl H  5-Br H       O 1 S     192 to 209                                     3-Cl H  5-Br H       O 1 S     175 to 190                                     4-Br H  5-Br H       O 1 S     188 to 215                                     4-Cl 3-Cl                                                                             5-Br H       O 1 S     187 to 200                                     4-CF.sub.3                                                                         H  4-Cl H       O 1 S     207 to 210                                     4-Cl H  4-Cl H       O 1 S     191 to 193                                     4-Br H  4-Cl H       O 1 S     188 to 190                                     4-CF.sub.3                                                                         H  H    Me      O 1 S                                                    4-CF.sub.2 Cl                                                                      3-Cl                                                                             5-Cl Me      O 2 S                                                    4-OCF.sub.3                                                                        H  5-Cl Me      O 0 S                                                    4-OCF.sub.2 H                                                                      H  5-F  Me      O 1 S                                                    4-Cl H  5-F  Me      O 2 S                                                    4-CO.sub.2 Me                                                                      H  H    Me      O 0 S                                                    4-Br H  H    Me      O 1 S                                                    4-CF.sub.3                                                                         H  5-Cl CO.sub.2 Me                                                                           O 2 S                                                    4-CF.sub.2 Cl                                                                      3-Cl                                                                             5-Cl CO.sub.2 Me                                                                           O 0 S                                                    4-OCF.sub.3                                                                        H  H    CO Me   O 1 S                                                    4-OCF.sub.2 H                                                                      H  H    CO.sub. 2 Me                                                                          O 2 S                                                    4-Cl H  5-Cl CO.sub.2 Me                                                                           O 0 S                                                    4-CO.sub.2 Me                                                                      H  5-Cl CO.sub.2 Me                                                                           O 1 S                                                    4-Br H  5-F  CO.sub.2 Me                                                                           O 2 S                                                    4-CF.sub.3                                                                         H  H    CO.sub.2 Et                                                                           O 0 S                                                    4-Cl H  H    CO.sub.2 CH.sub.2 CF.sub.3                                                            O 1 S                                                    4-CF.sub.3                                                                         H  5-Cl CH.sub.2 CF.sub.3                                                                     O 2 S                                                    4-Cl H  5-Cl C(O)Me  O 0 S                                                    4-CF.sub.3                                                                         H  5-OCF.sub.2 H                                                                      Me      O 1 S                                                    4-CF.sub.3                                                                         H  5-OCF.sub.2 H                                                                      CO.sub.2 Me                                                                           O 2 S                                                    4-Cl H  5-F  CONHMe  O 0 S                                                    4-CF.sub.3                                                                         H  5-F  CONHPh  O 1 S                                                    4-Cl H  H    allyl   O 2 S                                                    4-CF.sub.3                                                                         H  H    CH.sub.2 Ph                                                                           O 0 S                                                    4-Cl H  5-Cl n-Pr    O 1 S                                                    4-CF.sub.3                                                                         H  5-Cl C(O)(CH.sub.2).sub.3 Cl                                                               O 2 S                                                    4-Cl H  5-OCF.sub.2 H                                                                      Me      O 0 S                                                    4-CF.sub.3                                                                         H  5-OCF.sub.2 H                                                                      CO.sub.2 Me                                                                           O 1 S                                                    4-Cl H  5-F  CH.sub.2 CO.sub.2 Me                                                                  O 2 S                                                    4-CF.sub.3                                                                         H  5-F  CO.sub.2 H                                                                            O 0 S                                                    4-Cl H  H    4-Cl-Ph O 1 S                                                    4-CF.sub.3                                                                         H  H    4-Cl-Ph O 2 S                                                    4-Cl H  5-Cl CO.sub.2 Me                                                                           S 0 S                                                    4-CF.sub.3                                                                         H  5-Cl CO.sub.2 Me                                                                           S 1 S                                                    4-Cl H  5-OCF.sub.2 H                                                                      CO.sub.2 Me                                                                           S 2 S                                                    4-CF.sub.3                                                                         H  H    H       O 0 NMe                                                  4-CF.sub.2 Cl                                                                      3-Cl                                                                             H    H       O 1 NMe                                                  4-OCF.sub.3                                                                        H  5-Cl H       O 2 NMe                                                  4-OCF.sub.2 H                                                                      H  5-Cl H       O 0 NMe                                                  4-Cl H  5-F  H       O 1 NMe                                                  4-CO.sub.2 Me                                                                      H  5-F  H       O 2 NMe                                                  4-Br H  H    H       O 0 NMe                                                  4-CF.sub.3                                                                         H  H    Me      O 1 NMe                                                  4-CF.sub.2 Cl                                                                      3-Cl                                                                             5-Cl Me      O 2 NMe                                                  4-OCF.sub.3                                                                        H  5-Cl Me      O 0 NMe                                                  4-OCF.sub.2 H                                                                      H  5-F  Me      O 1 NMe                                                  4-Cl H  5-F  Me      O 2 NMe                                                  4-CO.sub.2 Me                                                                      H  H    Me      O 0 NMe                                                  4-Br H  H    Me      O 1 NMe                                                  4-CF.sub.3                                                                         H  5-Cl CO.sub.2 Me                                                                           O 2 NMe                                                  4-CF.sub.2 Cl                                                                      3-Cl                                                                             5-Cl CO.sub.2 Me                                                                           O 0 NMe                                                  4-OCF.sub.3                                                                        H  H    CO.sub.2 Me                                                                           O 1 NMe                                                  4-OCF.sub.2 H                                                                      H  H    CO.sub.2 Me                                                                           O 2 NMe                                                  4-Cl H  5-Cl CO.sub.2 Me                                                                           O 0 NMe                                                  4-CO.sub.2 Me                                                                      H  5-Cl CO.sub.2 Me                                                                           O 1 NMe                                                  4-Br H  5-F  CO.sub.2 Me                                                                           O 2 NMe                                                  4-CF.sub.3                                                                         H  H    CO.sub.2 Et                                                                           O 0 NMe                                                  4-Cl H  H    CO.sub.2 CH.sub.2 CF.sub.3                                                            O 1 NME                                                  4-CF.sub.3                                                                         H  5-Cl CH.sub.2 CF.sub.3                                                                     O 2 NMe                                                  4-Cl H  5-Cl C(O)Me  O 0 NMe                                                  4-CF.sub.3                                                                         H  5-OCF.sub.2 H                                                                      Me      O 1 NMe                                                  4-CF.sub.3                                                                         H  5-OCF.sub.2 H                                                                      CO.sub.2 Me                                                                           O 2 NMe                                                  4-Cl H  5-F  CONHMe  O 0 NMe                                                  4-CF.sub.3                                                                         H  5-F  CONHPh  O 1 NMe                                                  4-Cl H  H    allyl   O 2 NMe                                                  4-CF.sub.3                                                                         H  H    CH.sub.2 Ph                                                                           O 0 NMe                                                  4-Cl H  5-Cl n-Pr    O 1 NMe                                                  4-CF.sub.3                                                                         H  5-Cl C(O)(CH.sub.2).sub.3 Cl                                                               O 2 NMe                                                  4-Cl H  5-OCF.sub.2 H                                                                      Me      O 0 NMe                                                  4-CF.sub.3                                                                         H  5-OCF.sub.2 H                                                                      CO.sub.2 Me                                                                           O 1 NMe                                                  4-Cl H  5-F  CH.sub.2 CO.sub.2 Me                                                                  O 2 NMe                                                  4-CF.sub.3                                                                         H  5-F  CO.sub.2 H                                                                            O 0 NMe                                                  4-Cl H  H    4-Cl-Ph O 1 NMe                                                  4-CF.sub.3                                                                         H  H    4-Cl-Ph O 2 NMe                                                  4-Cl H  5-Cl CO.sub.2 Me                                                                           S 0 NMe                                                  4-CF.sub.3                                                                         H  5-Cl CO.sub.2 Me                                                                           S 1 NMe                                                  4-Cl H  5-OCF.sub.2 H                                                                      CO.sub.2 Me                                                                           S 2 NMe                                                  4-CF.sub.3                                                                         H  H    H       O 1 SO.sub.2                                                                            255 to 260                                     4-Cl 3-Cl                                                                             H    H       O 1 SO.sub.2                                                                            250 to 255                                     4-Br H  H    H       O 1 SO.sub.2                                                                            272 to 274                                     3-CF.sub.3                                                                         H  H    H       O 1 SO.sub.2                                                                            261 to 263                                     4-Cl H  H    H       O 1 SO.sub.2                                                                            247 to 250                                     3-Cl H  H    H       O 1 SO.sub.2                                                                            245 to 249                                     4-CF.sub.3                                                                         H  5-Cl H       O 1 SO.sub.2                                                                            293 to 297                                     3-CF.sub.3                                                                         H  5-Cl H       O 1 SO.sub.2                                                                            217 to 234                                     4-Cl H  5-Cl H       O 1 SO.sub.2                                                                            318 to 321                                     3-Cl H  5-Cl H       O 1 SO.sub.2                                                                            241 to 270                                     4-Br H  5-Cl H       O 1 SO.sub.2                                                                            290 to 292                                     4-Cl 3-Cl                                                                             5-Cl H       O 1 SO.sub.2                                                                            280 to 285                                     4-CF.sub.3                                                                         H  6-Cl H       O 1 SO.sub.2                                                                            290 to 292                                     3-CF.sub.3                                                                         H  6-Cl H       O 1 SO.sub.2                                                                            175 to 182                                     4-Cl H  6-Cl H       O 1 SO.sub.2                                                                            230 to 280                                     3-Cl H  6-Cl H       O 1 SO.sub.2                                                                            245 to 269                                     4-Br H  6-Cl H       O 1 SO.sub.2                                                                            307 to 310                                     4-Cl 3-Cl                                                                             6-Cl H       O 1 SO.sub.2                                                                            275 to 278                                     4-CF.sub.3                                                                         H  H    Me      O 0 SO.sub.2                                             4-Cl H  5-Cl Me      O 1 SO.sub.2                                             4-OCF.sub.3                                                                        H  H    Me      O 2 SO.sub.2                                             4-CF.sub.3                                                                         H  5-Cl CO.sub.2 Me                                                                           O 0 SO.sub.2                                             4-Cl H  H    CO.sub.2 Me                                                                           O 1 SO.sub.2                                             4-OCF.sub.3                                                                        H  5-Cl CO.sub.2 Me                                                                           O 2 SO.sub.2                                             3-CF.sub.3                                                                         H  H    H       O 1 SO(α)                                                                         255 to 260                                     4-CF.sub.3                                                                         H  H    H       O 1 SO(α)                                                                         250 to 255                                     4-Br H  H    H       O 1 SO(α)                                                                         278 to 282                                     4-Br H  H    H       O 1 SO(β)                                                                          258 to 260                                     4-Cl 3-Cl                                                                             H    H       O 1 SO(α)                                                                         275 to 280                                     4-Cl 3-Cl                                                                             H    H       O 1 SO(β)                                                                          265 to 269                                     4-Cl H  H    H       O 1 SO(α)                                                                         262 to 264                                     4-Cl H  H    H       O 1 SO(β)                                                                          247 to 250                                     3-Cl H  H    H       O 1 SO(α)                                                                         231 to 232                                     3-Cl H  H    H       O 1 SO(β)                                                                          255 to 258                                     4-CF.sub.3                                                                         H  5-Cl H       O 1 SO(α )                                                                        271 to 275                                     4-CF.sub.3                                                                         H  5-Cl H       O 1 SO(β)                                                                          256 to 277                                     3-CF.sub.3                                                                         H  5-Cl H       O 1 SO(α)                                                                         210 to 213                                     3-CF.sub.3                                                                         H  5-Cl H       O 1 SO(β)                                                                          250 to 252                                     4-Cl H  5-Cl H       O 1 SO(α)                                                                         284 to 286                                     4-Cl H  5-Cl H       O 1 SO(β)                                                                          278 to 283                                     3-Cl H  5-Cl H       O 1 SO(α)                                                                         240 to 241                                     3-Cl H  5-Cl H       O 1 SO(β)                                                                          230 to 246                                     4-Br H  5-Cl H       O 1 SO(α)                                                                         285 to 287                                     4-Br H  5-Cl H       O 1 SO(β)                                                                          267 to 272                                     4-Cl 3-Cl                                                                             5-Cl H       O 1 SO(α)                                                                         276 to 280                                     4-Cl 3-Cl                                                                             5-Cl H       O 1 SO(β)                                                                          254 to 268                                     4-CF.sub.3                                                                         H  6-Cl H       O 1 SO(α)                                                                         252 to 256                                     4-CF.sub.3                                                                         H  6-Cl H       O 1 SO(β)                                                                          218 to 232                                     3-CF.sub.3                                                                         H  6-Cl H       O 1 SO(α)                                                                         263 to 265                                     3-CF.sub.3                                                                         H  6-Cl H       O 1 SO(β)                                           4-Cl H  6-Cl H       O 1 SO(α)                                                                         243 to 245                                     4-Cl H  6-Cl H       O 1 SO(β)                                                                          269 to 272                                     3-Cl H  6-Cl H       O 1 SO(α)                                                                         154 to 160                                     3-Cl H  6-Cl H       O 1 SO(β)                                           4-Br H  6-Cl H       O 1 SO(α)                                                                         248 to 250                                     4-Br H  6-Cl H       O 1 SO(β)                                                                          283 to 285                                     4-Cl 3-Cl                                                                             6-Cl H       O 1 SO(α)                                                                         272 to 275                                     4-Cl 3-Cl                                                                             6-Cl H       O 1 SO(β)                                                                          289 to 295                                     3-CF.sub.3                                                                         H  H    H       O 1 SO(β)                                                                          229 to 236                                     4-CF.sub.3                                                                         H  H    H       O 1 SO(β)                                                                          235 to 258                                     4-OCF.sub.3                                                                        H  H    Me      O 0 N-n-Bu                                               4-CF.sub.3                                                                         H  5-Cl CO.sub.2 Me                                                                           O 1 N-allyl                                              4-Cl H  H    CO.sub.2 Me                                                                           O 0 N-Ph                                                 4-OCF.sub.3                                                                        H  5-Cl CO.sub.2 Me                                                                           O 1 N--CH.sub.2 Ph                                       4-CF.sub.3                                                                         H  H    CO.sub.2 Me                                                                           O 0 N-4-F-Ph                                             4-CF.sub.3                                                                         H  H    H       O 1 NH                                                   4-CF.sub.3                                                                         H  H    CO.sub.2 Me                                                                           O 1 NH                                                   4-CF.sub.3                                                                         H  5-Cl H       O 1 NMe                                                  4-CF.sub.3                                                                         H  5-Cl CO.sub.2 Me                                                                           O 1 NMe                                                  __________________________________________________________________________

                                      TABLE 3                                     __________________________________________________________________________                                   Phys.                                          R.sub.1.sup.a                                                                      R.sub.1.sup.b                                                                    R.sub.2                                                                            B       x t v     Prop. (m.p. °C.)                        __________________________________________________________________________    4-CF.sub.3                                                                         H  H    H       O 0 O                                                    4-CF.sub.2 Cl                                                                      3-Cl                                                                             H    H       O 1 O                                                    4-OCF.sub.3                                                                        H  5-Cl H       O 2 O                                                    4-OCF.sub.2 H                                                                      H  5-Cl H       O 2 O                                                    4-Cl H  5-F  H       O 1 O                                                    4-CO.sub.2 Me                                                                      H  5-F  H       O 2 O                                                    4-Br H  H    H       O 0 O                                                    4-CF.sub.3                                                                         H  H    Me      O 1 O                                                    4-CF.sub.2 Cl                                                                      3-Cl                                                                             5-Cl Me      O 2 O                                                    4-OCF.sub.3                                                                        H  5-Cl Me      O 0 O                                                    4-OCF.sub.2 H                                                                      H  5-F  Me      O 1 O                                                    4-Cl H  5-F  Me      O 2 O                                                    4-CO.sub.2 Me                                                                      H  H    Me      O 0 O                                                    4-Br H  H    Me      O 1 O                                                    4-CF.sub.3                                                                         H  5-Cl CO.sub.2 Me                                                                           O 2 O                                                    4-CF.sub.2 Cl                                                                      3-Cl                                                                             5-Cl CO.sub.2 Me                                                                           O 0 O                                                    4-OCF.sub.3                                                                        H  H    CO.sub.2 Me                                                                           O 1 O                                                    4-OCF.sub.2 H                                                                      H  H    CO.sub.2 Me                                                                           O 2 O                                                    4-Cl H  5-Cl CO.sub.2 Me                                                                           O 0 O                                                    4-CO.sub.2 Me                                                                      H  5-CL CO.sub.2 Me                                                                           O 1 O                                                    4-Br H  5-F  CO.sub.2 Me                                                                           O 2 O                                                    4-CF.sub.3                                                                         H  H    CO.sub.2 Et                                                                           O 0 O                                                    4-Cl H  H    CO.sub.2 CH.sub.2 CF.sub.3                                                            O 1 O                                                    4-CF.sub.3                                                                         H  5-CL CH.sub.2 CF.sub.3                                                                     O 2 O                                                    4-Cl H  5-Cl C(O)Me  O 0 O                                                    4-CF.sub.3                                                                         H  5-OCF.sub.2 H                                                                      Me      O 1 O                                                    4-CF.sub.3                                                                         H  5-OCF.sub.2 H                                                                      CO.sub.2 Me                                                                           O 2 O                                                    4-Cl H  5-F  CONHMe  O 0 O                                                    4-CF.sub.3                                                                         H  5-F  CONHPh  O 1 O                                                    4-Cl H  H    allyl   O 2 O                                                    4-CF.sub.3                                                                         H  H    CH.sub.2 Ph                                                                           O 0 O                                                    4-Cl H  5-Cl n-Pr    O 1 O                                                    4-CF.sub.3                                                                         H  5-Cl C(O)(CH.sub.2).sub.3 Cl                                                               O 2 O                                                    4-Cl H  5-OCF.sub.2 H                                                                      CO.sub.2 Me                                                                           O 1 O                                                    4-Cl H  5-F  CH.sub.2 CO.sub.2 Me                                                                  O 2 O                                                    4-CF.sub.3                                                                         H  5-F  CO.sub.2 H                                                                            O 0 O                                                    4-Cl H  H    4-Cl-Ph O 1 O                                                    4-CF.sub.3                                                                         H  H    4-Cl-Ph O 2 O                                                    4-Cl H  5-Cl CO.sub.2 Me                                                                           S 0 O                                                    4-CF.sub.3                                                                         H  5-Cl CO.sub.2 Me                                                                           S 1 O                                                    4-Cl H  5-OCF.sub.2 H                                                                      CO.sub.2 Me                                                                           S 2 O                                                    4-CF.sub.3                                                                         H  H    H       O 0 S                                                    4-CF.sub.2 Cl                                                                      3-Cl                                                                             H    H       O 1 S                                                    4-OCF.sub.3                                                                        H  5-Cl H       O 2 S                                                    4-OCF.sub.2 H                                                                      H  5-Cl H       O 2 S                                                    4-Cl H  5-F  H       O 1 S                                                    4-CO.sub.2 Me                                                                      H  5-F  H       O 2 S                                                    4-Br H  H    H       O 0 S                                                    4-CF.sub.3                                                                         H  H    Me      O 1 S                                                    4-CF.sub.2 Cl                                                                      3-Cl                                                                             5-Cl Me      O 2 S                                                    4-OCF.sub.3                                                                        H  5-Cl Me      O 0 S                                                    4-OCF.sub.2 H                                                                      H  5-F  Me      O 1 S                                                    4-Cl H  5-F  Me      O 2 S                                                    4-CO.sub.2 Me                                                                      H  H    Me      O 0 S                                                    4-Br H  H    Me      O 1 S                                                    4-CF.sub.3                                                                         H  5-Cl CO.sub.2 Me                                                                           O 2 S                                                    4-CF.sub.2 Cl                                                                      3-Cl                                                                             5-Cl CO.sub.2 Me                                                                           O 0 S                                                    4-OCF.sub.3                                                                        H  H    CO.sub.2 Me                                                                           O 1 S                                                    4-OCF.sub.2 H                                                                      H  H    CO.sub.2 Me                                                                           O 2 S                                                    4-Cl H  5-Cl CO.sub.2 Me                                                                           O 0 S                                                    4-CO.sub.2 Me                                                                      H  5-Cl CO.sub.2 Me                                                                           O 1 S                                                    4-Br H  5-F  CO.sub.2 Me                                                                           0 2 S                                                    4-CF.sub.3                                                                         H  H    CO.sub.2 Et                                                                           O 0 S                                                    4-Cl H  H    CO.sub.2 CH.sub.2 CF.sub.3                                                            O 1 S                                                    4-CF.sub.3                                                                         H  5-Cl CH.sub.2 CF.sub.3                                                                     O 2 S                                                    4-Cl H  5-Cl C(O)Me  O 0 S                                                    4-CF.sub.3                                                                         H  5-OCF.sub.2 H                                                                      Me      O 1 S                                                    4-CF.sub.3                                                                         H  5-OCF.sub.2 H                                                                      CO.sub.2 Me                                                                           O 2 S                                                    4-Cl H  5-F  CONHMe  O 0 S                                                    4-CF.sub.3                                                                         H  5-F  CONHPh  O 1 S                                                    4-Cl H  H    allyl   O 2 S                                                    4-CF.sub.3                                                                         H  H    CH.sub.2 Ph                                                                           O 0 S                                                    4-Cl H  5-Cl n-Pr    O 1 S                                                    4-CF.sub.3                                                                         H  5-Cl C(O)(CH.sub.2).sub.3 Cl                                                               O 2 S                                                    4-Cl H  5-OCF.sub.2 H                                                                      CO.sub.2 Me                                                                           O 1 S                                                    4-Cl H  5-F  CH.sub.2 CO.sub.2 Me                                                                  O 2 S                                                    4-CF.sub.3                                                                         H  5-F  CO.sub.2 H                                                                            O 0 S                                                    4-Cl H  H    4-Cl-Ph O 1 S                                                    4-CF.sub.3                                                                         H  H    4-Cl-Ph O 2 S                                                    4-Cl H  5-Cl CO.sub.2 Me                                                                           S 0 S                                                    4-CF.sub.3                                                                         H  5-Cl CO.sub.2 Me                                                                           S 1 S                                                    4-Cl H  5-OCF.sub.2 H                                                                      CO.sub.2 Me                                                                           S 2 S                                                    4-CF.sub.3                                                                         H  H    H       O 0 NMe                                                  4-CF.sub.2 Cl                                                                      3-Cl                                                                             H    H       O 1 NMe                                                  4-OCF.sub.3                                                                        H  5-Cl H       O 2 NMe                                                  4-OCF.sub.2 H                                                                      H  5-Cl H       O 2 NMe                                                  4-Cl H  5-F  H       O 1 NMe                                                  4-CO.sub.2 Me                                                                      H  5-F  H       O 2 NMe                                                  4-Br H  H    H       O 0 NMe                                                  4-CF.sub.3                                                                         3-Cl                                                                             5-Cl Me      O 1 NMe                                                  4-CF.sub.2 Cl                                                                      3-Cl                                                                             5-Cl Me      O 2 NMe                                                  4-OCF.sub.3                                                                        H  5-Cl Me      O 0 NMe                                                  4-OCF.sub.2 H                                                                      H  5-F  Me      O 1 NMe                                                  4-Cl H  5-F  Me      O 2 NMe                                                  4-CO.sub.2 Me                                                                      H  H    Me      O 0 NMe                                                  4-Br H  H    Me      O 1 NMe                                                  4-CF.sub.3                                                                         H  5-Cl CO.sub.2 Me                                                                           O 2 NMe                                                  4-CF.sub.2 Cl                                                                      3-Cl                                                                             5-Cl CO.sub.2 Me                                                                           O 0 NMe                                                  4-OCF.sub.3                                                                        H  H    CO.sub.2 Me                                                                           O 1 NMe                                                  4-OCF.sub.2 H                                                                      H  H    CO.sub.2 Me                                                                           O 2 NMe                                                  4-Cl H  5-Cl CO.sub.2 Me                                                                           O 0 NMe                                                  4-CO.sub.2 Me                                                                      H  5-Cl CO.sub.2 Me                                                                           O 1 NMe                                                  4-Br H  5-F  CO.sub.2 Me                                                                           O 2 NMe                                                  4-CF.sub.3                                                                         H  H    CO.sub.2 Et                                                                           O 0 NMe                                                  4-Cl H  H    CO.sub.2 CH.sub.2 CF.sub.3                                                            O 1 NMe                                                  4-CF.sub.3                                                                         H  5-Cl CH.sub.2 CF.sub.3                                                                     O 2 NMe                                                  4-Cl H  5-Cl C(O)Me  O 0 NMe                                                  4-CF.sub.3                                                                         H  5-OCF.sub.2 H                                                                      Me      O 1 NMe                                                  4-CF.sub.3                                                                         H  5-OCF.sub.2 H                                                                      CO.sub.2 Me                                                                           O 2 NMe                                                  4-Cl H  5-F  CONHMe  O 0 NMe                                                  4-CF.sub.3                                                                         H  5-F  CONHPh  O 1 NMe                                                  4-Cl H  H    allyl   O 2 NMe                                                  4-CF.sub.3                                                                         H  H    CH.sub.2 Ph                                                                           O 0 NMe                                                  4-Cl H  5-Cl N--Pr   O 1 NMe                                                  4-CF.sub.3                                                                         H  5-Cl C(O)(CH.sub.2).sub.3 Cl                                                               O 2 NMe                                                  4-Cl H  5-OCF.sub.2 H                                                                      CO.sub.2 Me                                                                           O 1 NMe                                                  4-Cl H  5-F  CH.sub.2 CO.sub.2 Me                                                                  O 2 NMe                                                  4-CF.sub.3                                                                         H  5-F  CO.sub.2 H                                                                            O 0 NMe                                                  4-Cl H  H    4-Cl-Ph O 1 NMe                                                  4-CF.sub.3                                                                         H  H    4-Cl-Ph O 2 NMe                                                  4-Cl H  5-Cl CO.sub.2 Me                                                                           S 0 NMe                                                  4-CF.sub.3                                                                         H  5-Cl CO.sub.2 Me                                                                           S 1 NMe                                                  4-Cl H  5-OCF.sub.2 H                                                                      CO.sub.2 Me                                                                           S 2 NMe                                                  4-CF.sub.3                                                                         H  H    Me      O 0 SO.sub.2                                             4-Cl H  5-Cl Me      O 1 SO.sub.2                                             4-OCF.sub.3                                                                        H  H    Me      O 2 SO.sub.2                                             4-CF.sub.3                                                                         H  5-Cl CO.sub. 2 Me                                                                          O 0 SO.sub.2                                             4-Cl H  H    CO.sub.2 Me                                                                           O 1 SO.sub.2                                             4-OCF.sub.3                                                                        H  5-Cl CO.sub.2 Me                                                                           O 2 SO.sub.2                                             4-CF.sub.3                                                                         H  H    Me      O 0 SO                                                   4-Cl H  5-Cl Me      O 1 SO                                                   4-OCF.sub.3                                                                        H  H    Me      O 2 SO                                                   4-CF.sub.3                                                                         H  5-Cl CO.sub.2 Me                                                                           O 0 SO                                                   4-Cl H  H    CO.sub.2 Me                                                                           O 1 SO                                                   4-OCF.sub.3                                                                        H  5-Cl CO.sub.2 Me                                                                           O 2 SO                                                   4-CF.sub.3                                                                         H  H    Me      O 0 SO                                                   4-Cl H  5-Cl Me      O 1 NH                                                   4-OCF.sub.3                                                                        H  H    Me      O 0 N-n-Bu                                               4-CF.sub.3                                                                         H  5-Cl CO.sub.2 Me                                                                           O 1 N-allyl                                              4-Cl H  H    CO.sub.2 Me                                                                           O 0 N-Ph                                                 4-OCH.sub.3                                                                        H  5-Cl CO.sub.2 Me                                                                           O 1 N--CH.sub.2 Ph                                       4-CF.sub.3                                                                         H  H    CO.sub.2 Me                                                                           O 0 N-4-F-Ph                                             __________________________________________________________________________

                  TABLE 4                                                         ______________________________________                                                                                 Phys.                                                                         Prop.                                R.sub.1.sup.a                                                                        R.sub.1.sup.b                                                                        R.sub.2  B      x   z      (m.p. °C.)                    ______________________________________                                        4-CF.sub.3                                                                           H      H        H      O   O                                           4-Cl   H      H        H      O   O                                           4-F    H      5-Cl     H      O   O                                           4-OCF.sub.2 H                                                                        H      5-Cl     Me     O   O                                           4-SMe  H      H        Me     O   O                                           4-Cl   3-Cl   H        Me     O   O                                           4-CF.sub.3                                                                           H      5-Cl     Et     O   O                                           4-Cl   H      5-Cl     Et     O   O                                           4-F    H      H        Et     O   O                                           4-OCF.sub.2 H                                                                        H      H        allyl  O   O                                           4-SMe  H      5-Cl     allyl  O   O                                           4-Cl   3-Cl   5-Cl     allyl  O   O                                           4-CF.sub.3                                                                           H      5-F      CO.sub.2 Me                                                                          O   O                                           4-Cl   H      5-F      C(O)Me O   O                                           4-F    H      5-OCF.sub.2 H                                                                          CH.sub.2 Ph                                                                          O   O                                           4-OCF.sub.2 H                                                                        H      5-OCF.sub.2 H                                                                          CH.sub.2 Ph                                                                          O   O                                           4-SMe  H      5-CF.sub.3                                                                             Ph     O   O                                           4-Cl   3-Cl   5-CF.sub.3                                                                             Ph     O   O                                           4-CF.sub.3                                                                           H      H        Me     S   O                                           4-Cl   H      H        Me     S   O                                           4-F    H      H        Me     S   O                                           4-CF.sub.3                                                                           H      H        H      O   NMe                                         4-Cl   H      H        H      O   NMe                                         4-F    H      5-Cl     H      O   NMe                                         4-OCF.sub.2 H                                                                        H      5-Cl     Me     O   NMe                                         4-SMe  H      H        Me     O   NMe                                         4-Cl   3-Cl   H        Me     O   NMe                                         4-CF.sub.3                                                                           H      5-Cl     Et     O   NMe                                         4-Cl   H      5-Cl     Et     O   NMe                                         4-F    H      H        Et     O   NMe                                         4-OCF.sub.2 H                                                                        H      H        allyl  O   NMe                                         4-SMe  H      5-Cl     allyl  O   NMe                                         4-Cl   3-Cl   5-Cl     allyl  O   NMe                                         4-CF.sub.3                                                                           H      5-F      CO.sub.2 Me                                                                          O   NMe                                         4-Cl   H      5-F      C(O)Me O   NMe                                         4-F    H      5-OCF.sub.2 H                                                                          CH.sub.2 Ph                                                                          O   NMe                                         4-OCF.sub.2 H                                                                        H      5-OCF.sub.2 H                                                                          CH.sub.2 Ph                                                                          O   NMe                                         4-SMe  H      5-CF.sub.3                                                                             Ph     O   NMe                                         4-Cl   3-Cl   5-CF.sub.3                                                                             Ph     O   NMe                                         4-CF.sub.3                                                                           H      H        Me     S   NMe                                         4-Cl   H      H        Me     S   NMe                                         4-F    H      H        Me     S   NMe                                         4-CF.sub.3                                                                           H      H        Me     O   NH                                          4-Cl   H      5-Cl     Me     O   NH                                          4-Br   H      5-F      Me     O   NH                                          4-OCF.sub.3                                                                          H      H        Me     O   NH                                          4-CF.sub.3                                                                           H      5-Cl     Me     O   NEt                                         4-Cl   H      5-F      Me     O   NEt                                         4-Br   H      H        Me     O   NEt                                         4-OCF.sub.3                                                                          H      5-Cl     Me     O   N-n-C.sub.4 H.sub.9                         4-CF.sub.3                                                                           H      5-F      Me     O   N-n-C.sub.4 H.sub.9                         4-Cl   H      H        Me     O   N-allyl                                     4-Br   H      5-Cl     Me     O   N-allyl                                     4-OCF.sub.3                                                                          H      5-F      Me     O   N-4-Cl--Ph                                  4-CF.sub.3                                                                           H      H        Me     O   N-4-F--Ph                                   4-Cl   H      5-Cl     Me     O   NPh                                         4-Br   H      5-F      Me     O   NCH.sub.2 Ph                                4-OCF.sub.3                                                                          H      H        Me     O   NCH.sub.2 Ph                                4-CF.sub.3                                                                           H      5-Cl     Me     O   N--CH.sub.2 C(Cl)═CH.sub.2              ______________________________________                                    

                  TABLE 5                                                         ______________________________________                                                                                   Phys.                                                                         Prop.                                                                         (m.p. -R.sub.1.sup.a R.sub.1.su                                               p.b R.sub.2 B x z °C.)      ______________________________________                                        4-CF.sub.3                                                                            H      H       H         O   O                                        4-OCF.sub.3                                                                           H      5-Cl    H         O   O                                        4-OCF.sub.2 H                                                                         H      H       H         O   O                                        4-Cl    H      5-Cl    CO.sub.2 Me                                                                             O   O                                        4-F     H      H       CO.sub.2 Me                                                                             O   O                                        4-Br    H      5-Cl    CO.sub.2 Me                                                                             O   O                                        4-CF.sub.3                                                                            H      H       CO.sub.2 Me                                                                             O   O                                        4-OCF.sub.3                                                                           H      5-Cl    CO.sub.2 Me                                                                             O   O                                        4-OCF.sub.2 H                                                                         H      H       CO.sub.2 Me                                                                             O   O                                        4-Cl    H      5-Cl    Me        O   O                                        4-F     H      H       Me        O   O                                        4-Br    H      5-Cl    Me        O   O                                        4-CF.sub.3                                                                            H      H       Et        O   O                                        4-OCF.sub.3                                                                           H      5-Cl    n-Pr      O   O                                        4-OCF.sub.2 H                                                                         H      H       allyl     O   O                                        4-Cl    H      5-Cl    allyl     O   O                                        4-F     H      H       CH.sub.2 -4-F--Ph                                                                       O   O                                        4-Br    H      5-Cl    CH.sub.2 -4-Cl--Ph                                                                      O   O                                        4-CF.sub.3                                                                            H      H       CH.sub.2 CF.sub.3                                                                       O   O                                        4-OCF.sub.3                                                                           H      5-Cl    (CH.sub.2).sub.4 Cl                                                                     O   O                                        4-OCF.sub.2 H                                                                         H      H       i-Pr      O   O                                        4-CF.sub.3                                                                            H      5-Cl    OH        O   O                                        4-OCF.sub.3                                                                           H      5-Cl    OAc       O   O                                        4-OCF.sub.2 H                                                                         3-Cl   5-Cl    OMe       O   O                                        4-Cl    H      5-Cl    C(O)CH.sub.3                                                                            O   O                                        4-F     H      5-Cl    C(O)NHMe  O   O                                        4-Br    H      5-Cl    C(S)NMe.sub.2                                                                           O   O                                        4-CF.sub.3                                                                            H      5-F     Me        O   O                                        4-OCF.sub.3                                                                           H      5-F     n-Bu      O   O                                        4-OCF.sub.2 H                                                                         3-Cl   5-F     alkyl     O   O                                        4-Cl    H      5-F     i-Pr      O   O                                        4-F     H      5-F     CH.sub.2 Ph                                                                             O   O                                        4-Br    H      5-F     Ph        O   O                                        4-CF.sub.3                                                                            H      5-CF.sub.3                                                                            CH.sub.2 CH.sub.2 F                                                                     O   O                                        4-OCF.sub.3                                                                           H      5-CF.sub.3                                                                            CH.sub.2 SCH.sub.3                                                                      O   O                                        4-OCF.sub.2 H                                                                         3-Cl   5-CF.sub.3                                                                            CH.sub.2 OCH.sub.3                                                                      O   O                                        4-Cl    H      5-CF.sub.3                                                                            CH.sub.2 CN                                                                             O   O                                        4-F     H      5-CF.sub.3                                                                            CH.sub.2 CO.sub.2 Me                                                                    O   O                                        4-Br    H      5-CF.sub.3                                                                            CS.sub.2 Me                                                                             O   O                                        4-CF.sub.3                                                                            H      H       Me        S   O                                        4-OCF.sub.3                                                                           H      H       Me        S   O                                        4-OCF.sub.2 H                                                                         3-Cl   H       Me        S   O                                        4-CF.sub.3                                                                            H      H       H         O   NMe                                      4-OCF.sub.3                                                                           H      5-Cl    H         O   NMe                                      4-OCF.sub.2 H                                                                         H      H       H         O   NMe                                      4-Cl    H      5-Cl    CO.sub. 2 Me                                                                            O   NMe                                      4-F     H      H       CO.sub.2 Me                                                                             O   NMe                                      4-Br    H      5-Cl    CO.sub.2 Me                                                                             O   NMe                                      4-CF.sub.3                                                                            H      H       CO.sub.2 Me                                                                             O   NMe                                      4-OCF.sub.3                                                                           H      5-Cl    CO.sub.2 Me                                                                             O   NMe                                      4-OCF.sub.2 H                                                                         H      H       CO.sub.2 Me                                                                             O   NMe                                      4-Cl    H      5-Cl    Me        O   NMe                                      4-F     H      H       Me        O   NMe                                      4-Br    H      5-Cl    Me        O   NMe                                      4-CF.sub.3                                                                            H      H       Et        O   NMe                                      4-OCF.sub.2 H                                                                         H      H       allyl     O   NMe                                      4-Cl    H      5-Cl    allyl     O   NMe                                      4-F     H      H       CH.sub.2 -4-F--Ph                                                                       O   NMe                                      4-Br    H      5-Cl    CH.sub.2 -4-Cl--Ph                                                                      O   NMe                                      4-CF.sub.3                                                                            H      H       CH.sub.2 CF.sub.3                                                                       O   NMe                                      4-OCF.sub.3                                                                           H      5-Cl    (CH.sub.2).sub.4 Cl                                                                     O   NMe                                      4-OCF.sub.2 H                                                                         H      H       i-Pr      O   NMe                                      4-CF.sub.3                                                                            H      5-Cl    OH        O   NMe                                      4-OCF.sub.3                                                                           H      5-Cl    OAc       O   NMe                                      4-OCF.sub.2 H                                                                         3-Cl   5-Cl    OMe       O   NMe                                      4-Cl    H      5-Cl    C(O)CH.sub.3                                                                            O   NMe                                      4-F     H      5-Cl    C(O)NHMe  O   NMe                                      4-Br    H      5-Cl    C(S)NMe.sub.2                                                                           O   NMe                                      4-CF.sub.3                                                                            H      5-F     Me        O   NMe                                      4-OCF.sub.3                                                                           H      5-F     n-Bu      O   NMe                                      4-OCF.sub.2 H                                                                         3-Cl   5-F     allyl     O   NMe                                      4-Cl    H      5-F     i-Pr      O   NMe                                      4-F     H      5-F     CH.sub.2 Ph                                                                             O   NMe                                      4-Br    H      5-F     Ph        O   NMe                                      4-CF.sub.3                                                                            H      5-CF.sub.3                                                                            CH.sub.2 CH.sub.2 F                                                                     O   NMe                                      4-OCF.sub.3                                                                           H      5-CF.sub.3                                                                            CH.sub.2 OCH.sub.3                                                                      O   NMe                                      4-OCF.sub.2 H                                                                         3-Cl   5-CF.sub.3                                                                            CH.sub.2 OCH.sub.3                                                                      O   NMe                                      4-Cl    H      5-CF.sub.3                                                                            CH.sub.2 CN                                                                             O   NMe                                      4-F     H      5-CF.sub.3                                                                            CH.sub.2 CO.sub.2 Me                                                                    O   NMe                                      4-Br    H      5-CF.sub.3                                                                            CS.sub.2 Me                                                                             O   NMe                                      4-CF.sub.3                                                                            H      H       Me        S   NMe                                      4-OCF.sub.3                                                                           H      H       Me        S   NMe                                      4-OCF.sub.2 H                                                                         3-Cl   H       Me        S   NMe                                      4-CF.sub.3                                                                            H      H       Me        O   NEt                                      4-CF.sub.3                                                                            H      5-F     CO.sub.2 Me                                                                             O   NEt                                      4-CF.sub.3                                                                            H      5-Cl    Me        O   N-n-Bu                                   4-CF.sub.3                                                                            H      H       CO.sub.2 Me                                                                             O   N-n-Bu                                   4-CF.sub.3                                                                            H      5-F     Me        O   N-allyl                                  4-CF.sub.3                                                                            H      5-Cl    CO.sub.2 Me                                                                             O   N-allyl                                  4-CF.sub.3                                                                            H      H       Me        O   N--Ph                                    4-CF.sub.3                                                                            H      5-F     CO.sub.2 Me                                                                             O   N--Ph                                    4-CF.sub.3                                                                            H      5-Cl    Me        O   N-4-Cl--Ph                               4-CF.sub.3                                                                            H      H       CO.sub.2 Me                                                                             O   N-4-Cl--Ph                               ______________________________________                                    

                  TABLE 6                                                         ______________________________________                                                                Phys.                                                                         Prop.                                                 R.sub.1                                                                              R.sub.2                                                                              B           t   y       (m.p. °C.)                       ______________________________________                                        4-CF.sub.3                                                                           H      H           0   Me                                              4-Cl   H      Me          0   C(O)Me                                          4-OCF.sub.2 H                                                                        H      CO.sub.2 Me 0   n-Bu                                            4-CF.sub.3                                                                           H      C(O)Me      0   SMe                                             4-Cl   H      CO.sub.2 Et 0   SCCl.sub.3                                      4-OCF.sub.3                                                                          H      H           1   Me                                              4-CF.sub.3                                                                           H      H           1   C(O)Me  oil                                     4-F    H      CO.sub.2 Me 1   Me                                              4-OCF.sub.2 H                                                                        H      CO.sub.2 Me 1   C(O)Me                                          4-CF.sub.3                                                                           H      Me          1   C(O)CF.sub.3                                    4-Cl   H      Me          1   CO.sub.2 Et                                     4-CF.sub.3                                                                           H      CO.sub.2 CH.sub.2 CF.sub.3                                                                1   Me                                              4-OCF.sub.2 H                                                                        H      CO.sub.2 Et 1   Me                                              4-OCF.sub.3                                                                          H      CO.sub.2 CH.sub.2 CH.sub.2 Cl                                                             1   Me                                              4-Br   H      CONHMe      1   Me                                              4-SCF.sub.2 H                                                                        H      H           2   2-NO.sub.2 PhS                                  4-CF.sub.3                                                                           H      Me          2   CO.sub.2 Me                                     4-Cl   H      Me          2   C(O)Me                                          4-CF.sub.3                                                                           H      CO.sub.2 Me 2   C(O)Me                                          4-Cl   H      CO.sub.2 Me 2   Me                                              4-CF.sub.3                                                                           H      CO.sub.2 Me 1   C(O)Me  110 to 115                              4-CF.sub.3                                                                           H      CO.sub.2 Me 1   Me      glass                                   4-CF.sub.3                                                                           H      CO.sub.2 Me 1   CO.sub.2 Me                                                                           glass                                   4-CF.sub.3                                                                           5-Cl   CO.sub.2 Me 1   C(O)Me                                          4-CF.sub.3                                                                           5-Cl   CO.sub.2 Me 1   Me                                              4-CF.sub.3                                                                           5-Cl   CO.sub.2 Me 1   CO.sub.2 Me                                     4-CF.sub.3                                                                           4-F    CO.sub.2 Me 1   C(O)Me                                          4-CF.sub.3                                                                           5-F    CO.sub.2 Me 1   C(O)Me                                          4-CF.sub.3                                                                           4-F    CO.sub.2 Me 1   CO.sub.2 Me                                     4-CF.sub.3                                                                           5-F    CO.sub.2 Me 1   CO.sub.2 Me                                     4-CF.sub.3                                                                           H      H           1   CO.sub.2 -t-Bu                                                                        178 to 179                              ______________________________________                                    

                  TABLE 7                                                         ______________________________________                                                                Phys.                                                                         Prop.                                                 R.sub.1                                                                             R.sub.2  B        t   y      v    (m.p. °C.)                     ______________________________________                                        4-CF.sub.3                                                                          H        Me       0   Me     O                                          4-CF.sub.3                                                                          H        Me       1   Me     NMe                                        4-CF.sub.3                                                                          5-Cl     CO.sub.2 Me                                                                            2   Me     S                                          4-CF.sub.3                                                                          5-Cl     CO.sub.2 Me                                                                            0   Me     O                                          4-CF.sub.3                                                                          5-Cl     Me       1   Me     NMe                                        4-CF.sub.3                                                                          5-Cl     Me       2   C(O)Me S                                          4-CF.sub.3                                                                          5-F      CO.sub.2 Me                                                                            0   C(O)Me O                                          4-CF.sub.3                                                                          5-F      CO.sub.2 Me                                                                            1   C(O)Me NMe                                        4-CF.sub.3                                                                          5-F      Me       2   C(O)Me SO                                         4-CF.sub.3                                                                          5-F      Me       0   C(O)Me SO.sub.2                                   4-CF.sub.3                                                                          H        CO.sub.2 Me                                                                            1   SCCl.sub.3                                                                           O                                          4-CF.sub.3                                                                          H        CO.sub.2 Me                                                                            2   SCCl.sub.3                                                                           NMe                                        4-CF.sub.3                                                                          H        Me       0   CO.sub.2 Me                                                                          S                                          4-CF.sub.3                                                                          H        Me       1   CO.sub.2 Me                                                                          O                                          4-CF.sub.3                                                                          5-OCF.sub.2 H                                                                          CO.sub.2 Me                                                                            2   n-Pr   NMe                                        4-CF.sub.3                                                                          5-OCF.sub.2 H                                                                          CO.sub.2 Me                                                                            0   n-Pr   S                                          4-CF.sub.3                                                                          5-CF.sub.3                                                                             Me       1   C(O)CF.sub.3                                                                         O                                          4-CF.sub.3                                                                          5-CF.sub.3                                                                             Me       2   C(O)CF.sub.3                                                                         NMe                                        4-CF.sub.3                                                                          5-Cl     CO.sub.2 Me                                                                            0   SMe    S                                          4-CF.sub. 3                                                                         5-Cl     CO.sub.2 Me                                                                            1   SMe    O                                          4-CF.sub.3                                                                          H        H        1   Me     S    151 to 152                            4-CF.sub.3                                                                          H        H        1   CO.sub.2 Me                                                                          S    150 to 158                            4-CF.sub.3                                                                          H        H        1   C(O)Me S     80 to 85                             4-CF.sub.3                                                                          5-Cl     H        1   C(O)Me S     97 to 99                             4-CF.sub.3                                                                          5-CL     H        1   CO.sub.2 Me                                                                          S    170 to 172                            4-CF.sub.3                                                                          5-Cl     H        1   Me     S    180 to 183                            4-Cl  H        H        1   C(O)Me S    140 to 150                            4-Cl  H        H        1   Me     S    125 to 127                            4-Cl  5-Cl     H        1   C(O)Me S    127 to 142                            4-Cl  5-Cl     H        1   Me     S    160 to 165                            ______________________________________                                    

                  TABLE 8                                                         ______________________________________                                                                Phys.                                                                         Prop.                                                 R.sub.1                                                                             R.sub.2  B        t   y      v    (m.p. °C.)                     ______________________________________                                        4-CF.sub.3                                                                          H        Me       0   Me     O                                          4-CF.sub.3                                                                          H        Me       1   Me     NMe                                        4-CF.sub.3                                                                          5-Cl     CO.sub.2 Me                                                                            2   Me     S                                          4-CF.sub.3                                                                          5-Cl     CO.sub.2 Me                                                                            0   Me     O                                          4-CF.sub.3                                                                          5-Cl     Me       1   Me     NMe                                        4-CF.sub.3                                                                          5-Cl     Me       2   C(O)Me S                                          4-CF.sub.3                                                                          5-F      CO.sub.2 Me                                                                            0   C(O)Me O                                          4-CF.sub.3                                                                          5-F      CO.sub.2 Me                                                                            1   C(O)Me NMe                                        4-CF.sub.3                                                                          5-F      Me       2   C(O)Me SO                                         4-CF.sub.3                                                                          5-F      Me       0   C(O)Me SO.sub.2                                   4-CF.sub.3                                                                          H        CO.sub.2 Me                                                                            1   SCCl.sub.3                                                                           O                                          4-CF.sub.3                                                                          H        CO.sub.2 Me                                                                            2   SCCl.sub.3                                                                           NMe                                        4-CF.sub.3                                                                          H        Me       0   CO.sub.2 Me                                                                          S                                          4-CF.sub.3                                                                          H        Me       1   CO.sub.2 Me                                                                          O                                          4-CF.sub.3                                                                          5-OCF.sub.2 H                                                                          CO.sub.2 Me                                                                            2   n-Pr   NMe                                        4-CF.sub.3                                                                          5-OCF.sub.2 H                                                                          CO.sub.2 Me                                                                            0   n-Pr   S                                          4-CF.sub.3                                                                          5-CF.sub.3                                                                             Me       1   C(O)CF.sub.3                                                                         O                                          4-CF.sub.3                                                                          5-CF.sub.3                                                                             Me       2   C(O)CF.sub.3                                                                         NMe                                        4-CF.sub.3                                                                          5-Cl     CO.sub.2 Me                                                                            0   SMe    S                                          4-CF.sub.3                                                                          5-Cl     CO.sub.2 Me                                                                            1   SMe    O                                          ______________________________________                                    

                  TABLE 9                                                         ______________________________________                                                                             Phys.                                    R.sub.1                                                                             R.sub.2  B        y       z    Prop. (m.p. °C.)                  ______________________________________                                        4-CF.sub.3                                                                          H        Me       Me      O                                             4-Cl  H        Me       C(O)Me  NMe                                           4-CF.sub.3                                                                          H        Me       Et      O                                             4-Cl  5-Cl     Me       CO.sub.2 Me                                                                           NMe                                           4-CF.sub.3                                                                          5-Cl     Et       n-Pr    O                                             4-Cl  5-F      Et       CO.sub.2 Et                                                                           NMe                                           4-CF.sub.3                                                                          5-F      Et       C(O)Me  O                                             4-Cl  5-Cl     Et       S--CCl.sub.3                                                                          NMe                                           4-CF.sub.3                                                                          5-Cl     (CH.sub.2).sub.3 Cl                                                                    SPh     O                                             4-Cl  H        (CH.sub.2).sub.3 Cl                                                                    Me      NMe                                           4-CF.sub.3                                                                          H        CH.sub.2 Ph                                                                            Me      O                                             4-Cl  H        CH.sub.2 Ph                                                                            C(O)Me  NMe                                           4-CF.sub.3                                                                          5-OCF.sub.3                                                                            Ph       C(O)CF.sub.3                                                                          O                                             4-Cl  5-OMe    Ph       2-NO.sub.2 PhS                                                                        NMe                                           4-CF.sub.3                                                                          5-Cl     4-Cl--Ph Me      O                                             4-Cl  5-F      4-Cl--Ph Et      NMe                                           4-CF.sub.3                                                                          H        allyl    C(O)Me  O                                             4-Cl  H        allyl    CO.sub.2 Et                                                                           NMe                                           4-CF.sub.3                                                                          5-Cl     OH       SCCl.sub.3                                                                            O                                             4-Cl  H        OH       Me      NMe                                           4-CF.sub.3                                                                          H        OAc      C(O)Me  O                                             4-Cl  H        OAc      Me      NMe                                           ______________________________________                                    

                  TABLE 10                                                        ______________________________________                                                                             Phys.                                    R.sub.1                                                                             R.sub.2  B        y       z    Prop. (m.p. °C.)                  ______________________________________                                        4-CF.sub.3                                                                          H        Me       Me      O                                             4-Cl  H        Me       C(O)Me  NMe                                           4-CF.sub.3                                                                          H        Me       Et      O                                             4-Cl  5-Cl     Me       CO.sub.2 Me                                                                           NMe                                           4-CF.sub.3                                                                          5-Cl     Et       n-Pr    O                                             4-Cl  5-F      Et       CO.sub.2 Et                                                                           NMe                                           4-CF.sub.3                                                                          5-F      Et       C(O)Me  O                                             4-Cl  5-Cl     Et       S--CCl.sub.3                                                                          NMe                                           4-CF.sub.3                                                                          5-Cl     (CH.sub.2).sub.3 Cl                                                                    SPh     O                                             4-Cl  H        (CH.sub.2).sub.3 Cl                                                                    Me      NMe                                           4-CF.sub.3                                                                          H        CH.sub.2 Ph                                                                            Me      O                                             4-Cl  H        CH.sub.2 Ph                                                                            C(O)Me  NMe                                           4-CF.sub.3                                                                          5-OCF.sub.3                                                                            Ph       C(O)CF.sub.3                                                                          O                                             4-Cl  5-OMe    Ph       2-NO.sub.2 PhS                                                                        NMe                                           4-CF.sub.3                                                                          5-Cl     4-Cl--Ph Me      O                                             4-Cl  5-F      4-Cl--Ph Et      NMe                                           4-CF.sub.3                                                                          H        allyl    C(O)Me  O                                             4-Cl  H        allyl    CO.sub.2 Et                                                                           NMe                                           4-CF.sub.3                                                                          5-Cl     OH       SCCl.sub.3                                                                            O                                             4-Cl  H        OH       Me      NMe                                           4-CF.sub.3                                                                          H        OAc      C(O)Me  O                                             4-Cl  H        OAc      Me      NMe                                           ______________________________________                                    

                  TABLE 11                                                        ______________________________________                                                                                 Prop.                                                                         Prop.                                R.sub.1                                                                             R.sub.2  B        t   J       K    (m.p. °C.)                    ______________________________________                                        4-CF.sub.3                                                                          H        H        0   Me      H                                         4-Cl  H        H        1   Me      H                                         4-CF.sub.3                                                                          H        Me       2   Me      H                                         4-Cl  5-Cl     Me       0   Ph      H                                         4-CF.sub.3                                                                          5-Cl     CO.sub.2 Me                                                                            1   Ph      H                                         4-Cl  5-Cl     CO.sub.2 Me                                                                            2   4-Cl--Ph                                                                              H                                         4-CF.sub.3                                                                          H        H        0   4-F--Ph H                                         4-Cl  H        H        1   4-CF.sub.3 --Ph                                                                       H                                         4-CF.sub.3                                                                          H        Me       2   Et      H                                         4-Cl  5-F      Me       0   n-Pr    H                                         4-CF.sub.3                                                                          5-F      CO.sub.2 Me                                                                            1   n-Bu    H                                         4-Cl  5-F      CO.sub.2 Me                                                                            2   Me      Me                                        4-CF.sub.3                                                                          H        H        0   Me      Me                                        4-Cl  H        H        1   Me      Me                                        4-CF.sub.3                                                                          H        Me       2   Me      Me                                        4-Cl  5-Cl     Me       0   Ph      Me                                        4-CF.sub.3                                                                          5-Cl     CO.sub.2 Me                                                                            1   Ph      Me                                        4-Cl  5-Cl     CO.sub.2 Me                                                                            2   Ph      Me                                        4-CF.sub.3                                                                          H        H        0   Ph      Me                                        4-Cl  H        H        1   Et      Me                                        4-CF.sub.3                                                                          H        Me       2   n-Pr    Me                                        4-Cl  H        Me       0   n-Bu    Me                                        4-CF.sub.3                                                                          H        H        1   4-F--Ph H    199 to 201                           4-CF.sub.3                                                                          H        H        1   4-Cl--Ph                                                                              H    187 to 188                           4-CF.sub.3                                                                          5-Cl     H        1   4-F--Ph H                                         4-CF.sub.3                                                                          5-Cl     H        1   4-Cl--Ph                                                                              H                                         4-CF.sub.3                                                                          4-F      H        1   4-F--Ph H                                         4-CF.sub.3                                                                          4-F      H        1   4-Cl--Ph                                                                              H                                         4-CF.sub.3                                                                          5-OCF.sub.2 H                                                                          H        1   4-F--Ph H                                         4-CF.sub.3                                                                          5-OCF.sub.2 H                                                                          H        1   4-Cl--Ph                                                                              H                                         4-Cl  H        H        1   4-F--Ph H    208 to 209                           4-Cl  H        H        1   4-Cl--Ph                                                                              H    179 to 181                           ______________________________________                                    

                  TABLE 12                                                        ______________________________________                                                                                    Phys.                                                                         Prop.                             R.sub.1                                                                             R.sub.2                                                                              B        t    J      K    V    (m.p. °C.)                 ______________________________________                                        4-CF.sub.3                                                                          H      H        0    Me     H    O                                      4-CF.sub.3                                                                          H      Me       1    Me     H    O                                      4-CF.sub.3                                                                          4-F    Et       2    Ph     H    O                                      4-CF.sub.3                                                                          H      CO.sub.2 Me                                                                            0    Ph     Me   O                                      4-CF.sub.3                                                                          H      CO.sub.2 Et                                                                            1    Me     Me   O                                      4-CF.sub.3                                                                          H      H        2    Me     Me   O                                      4-CF.sub.3                                                                          4-Cl   Me       0    4-Cl--Ph                                                                             Me   O                                      4-CF.sub.3                                                                          H      Et       1    Me     H    S                                      4-CF.sub.3                                                                          H      CO.sub.2 Me                                                                            2    Me     H    S                                      4-CF.sub.3                                                                          4-Br   CO.sub.2 Et                                                                            0    Ph     H    S                                      4-CF.sub.3                                                                          H      H        1    Ph     Me   S                                      4-CF.sub.3                                                                          H      Me       2    Me     Me   S                                      4-CF.sub.3                                                                          H      Et       0    Me     Me   S                                      4-CF.sub.3                                                                          H      CO.sub.2 Me                                                                            1    4-F--Ph                                                                              Me   S                                      4-CF.sub.3                                                                          H      CO.sub.2 Et                                                                            2    Me     H    NMe                                    4-CF.sub.3                                                                          H      H        0    Me     H    NMe                                    4-CF.sub.3                                                                          5-Cl   Me       1    Ph     H    NMe                                    4-CF.sub. 3                                                                         H      Et       2    Ph     Me   NMe                                    4-CF.sub.3                                                                          5-Me   CO.sub.2 Me                                                                            0    Me     Me   NMe                                    4-CF.sub.3                                                                          H      CO.sub.2 Et                                                                            1    Me     Me   NMe                                    4-CF.sub.3                                                                          H      H        2    4-Cl--Ph                                                                             Me   NMe                                    ______________________________________                                    

                  TABLE 13                                                        ______________________________________                                                                                    Phys.                                                                         Prop.                             R.sub.1                                                                             R.sub.2                                                                              B        t    J      K    V    (m.p. °C.)                 ______________________________________                                        4-CF.sub.3                                                                          H      H        0    Me     H    O                                      4-CF.sub.3                                                                          H      Me       1    Me     H    O                                      4-CF.sub.3                                                                          4-F    Et       2    Ph     H    O                                      4-CF.sub.3                                                                          H      CO.sub.2 Me                                                                            0    Ph     Me   O                                      4-CF.sub.3                                                                          H      CO.sub.2 Et                                                                            1    Me     Me   O                                      4-CF.sub.3                                                                          H      H        2    Me     Me   O                                      4-CF.sub.3                                                                          4-Cl   Me       0    4-Cl--Ph                                                                             Me   O                                      4-CF.sub.3                                                                          H      Et       1    Me     H    S                                      4-CF.sub.3                                                                          H      CO.sub.2 Me                                                                            2    Me     H    S                                      4-CF.sub.3                                                                          4-Br   CO.sub.2 Et                                                                            0    Ph     H    S                                      4-CF.sub.3                                                                          H      H        1    Ph     Me   S                                      4-CF.sub.3                                                                          H      Me       2    Me     Me   S                                      4-CF.sub.3                                                                          H      Et       0    Me     Me   S                                      4-CF.sub.3                                                                          H      CO.sub.2 Me                                                                            1    4-F--Ph                                                                              Me   S                                      4-CF.sub.3                                                                          H      CO.sub.2 Et                                                                            2    Me     H    NMe                                    4-CF.sub.3                                                                          H      H        0    Me     H    NMe                                    4-CF.sub.3                                                                          5-Cl   Me       1    Ph     H    NMe                                    4-CF.sub. 3                                                                         H      Et       2    Ph     Me   NMe                                    4-CF.sub.3                                                                          5-Me   CO.sub.2 Me                                                                            0    Me     Me   NMe                                    4-CF.sub.3                                                                          H      CO.sub.2 Et                                                                            1    Me     Me   NMe                                    4-CF.sub.3                                                                          H      H        2    4-Cl--Ph                                                                             Me   NMe                                    ______________________________________                                    

                  TABLE 14                                                        ______________________________________                                                                                Phys.                                                                         Prop.                                 R.sub.1                                                                              R.sub.2                                                                              B         J     K    Z    (m.p. °C.)                     ______________________________________                                        4-CF.sub.3                                                                           H      H         Me    H    O                                          4-Cl   H      Me        Me    Me   O                                          4-OCF.sub.2 H                                                                        H      Me        Ph    H    O                                          4-CF.sub.3                                                                           H      allyl     4-Cl--Ph                                                                            Me   NMe                                        4-Cl   H      allyl     Me    H    NMe                                        4-OCF.sub.2 H                                                                        5-F    CH.sub.2 Ph                                                                             4-F--Ph                                                                             Me   NMe                                        4-CF.sub.3                                                                           H      CH.sub.2 Ph                                                                             Me    H    O                                          4-Cl   H      Ph        Me    Me   O                                          4-OCF.sub.2 H                                                                        H      Ph        Ph    H    O                                          4-CF.sub.3                                                                           H      4-F--Ph   Ph    Me   NMe                                        4-Cl   H      4-F--Ph   Me    H    NMe                                        4-OCF.sub.2 H                                                                        5-Cl   OH        Me    Me   NMe                                        4-CF.sub.3                                                                           H      OH        Me    H    O                                          4-Cl   H      OMe       Et    Me   O                                          4-OCF.sub.2 H                                                                        H      OMe       Ph    H    O                                          4-CF.sub.3                                                                           H      CO.sub.2 Et                                                                             4-Cl--Ph                                                                            Me   NMe                                        4-Cl   H      CO.sub.2 Et                                                                             Me    H    NMe                                        4-OCF.sub.2 H                                                                        5-Cl   CONHMe    Ph    Me   NMe                                        4-CF.sub.3                                                                           H      CONHMe    Me    H    O                                          4-Cl   H      n-Bu      Ph    Me   H    O                                     4-OCF.sub.2 H                                                                        H      n-Bu      Me    H    O                                          ______________________________________                                    

                  TABLE 15                                                        ______________________________________                                                                                Phys.                                                                         Prop.                                 R.sub.1                                                                              R.sub.2                                                                              B        J      K    Z    (m.p. °C.)                     ______________________________________                                        4-CF.sub.3                                                                           H      Me       Me     H    O                                          4-Cl   H      CO.sub.2 Me                                                                            Me     H    O                                          4-OCF.sub.2 H                                                                        H      H        Me     H    O                                          4-CF.sub.3                                                                           H      Me       Ph     H    O                                          4-Cl   H      CO.sub.2 Me                                                                            Ph     H    O                                          4-OCF.sub.2 H                                                                        H      H        Ph     H    O                                          4-CF.sub.3                                                                           5-Cl   Et       4-Cl--Ph                                                                             H    NMe                                        4-Cl   H      CO.sub.2 Et                                                                            4-Cl--Ph                                                                             H    NMe                                        4-COF.sub.2 H                                                                        H      (CH.sub.2).sub.3 Cl                                                                    4-Cl--Ph                                                                             H    NMe                                        4-CF.sub.3                                                                           H      Me       Me     H    NMe                                        4-Cl   H      H        Me     H    NMe                                        4-OCF.sub.2 H                                                                        H      CO.sub.2 Me                                                                            Me     Me   O                                          4-CF.sub.3                                                                           H      H        Me     Me   O                                          4-Cl   H      Me       Me     Me   O                                          4-OCF.sub.2 H                                                                        5-F    C(O)Me   Ph     Me   O                                          4-CH.sub.3                                                                           H      C(O)Et   Ph     Me   O                                          4-Cl   H      Me       Me     Me   NMe                                        4-OCF.sub.2 H                                                                        H      Et       Me     Me   NMe                                        4-CF.sub.3                                                                           H      n-Pr     Ph     Me   NMe                                        4-Cl   H      CO.sub.2 Me                                                                            Ph     Me   NMe                                        4-OCF.sub.2 H                                                                        H      Me       4-Cl--Ph                                                                             Me   NMe                                        4-CF.sub.3                                                                           H      Et       4-Cl--Ph                                                                             Me   NMe                                        ______________________________________                                    

                                      TABLE 16                                    __________________________________________________________________________                                   Phys.                                          R.sub.1                                                                            R.sub.2                                                                            B    R.sub.8.sup.a                                                                    R.sub.8.sup.b                                                                    R.sub.8.sup.c                                                                      R.sub.8.sup.d                                                                      Prop. (m.p. °C.)                        __________________________________________________________________________    4-CF.sub.3                                                                         H    H    Me H  H    H                                                   4-Cl H    H    Me H  H    H                                                   4-Br H    H    Me H  H    H                                                   4-OCF.sub.2 H                                                                      H    H    Me H  H    H                                                   4-CF.sub.3                                                                         H    CO.sub.2 Me                                                                        Me H  H    H                                                   4-Cl H    CO.sub.2 Me                                                                        Me H  H    H                                                   4-Br H    CO.sub.2 Me                                                                        Me H  H    H                                                   4-OCF.sub.2 H                                                                      H    CO.sub.2 Me                                                                        Me H  H    H                                                   4-CF.sub.3                                                                         5-Cl H    Me H  H    H                                                   4-Cl 5-Cl H    Me H  H    H                                                   4-Br 5-Cl H    Me H  H    H                                                   4-OCF.sub.2 H                                                                      5-Cl H    Me H  H    H                                                   4-CF.sub.3                                                                         5-Cl CO.sub.2 Me                                                                        Me H  H    H                                                   4-Cl 5-Cl CO.sub.2 Me                                                                        Me H  H    H                                                   4-Br 5-Cl CO.sub.2 Me                                                                        Me H  H    H                                                   4-OCF.sub.2 H                                                                      5-Cl CO.sub.2 Me                                                                        Me H  H    H                                                   4-CF.sub.3                                                                         4-F  H    Me H  H    H                                                   4-Cl 4-F  H    Me H  H    H                                                   4-Br 4-F  H    Me H  H    H                                                   4-OCF.sub.2 H                                                                      4-F  H    Me H  H    H                                                   4-CF.sub.3                                                                         4-F  CO.sub.2 Me                                                                        Me H  H    H                                                   4-Cl 4-F  CO.sub.2 Me                                                                        Me H  H    H                                                   4-Br 4-F  CO.sub.2 Me                                                                        Me H  H    H                                                   4-OCF.sub.2 H                                                                      4-F  CO.sub.2 Me                                                                        Me H  H    H                                                   4-CF.sub.3                                                                         H    H    Me Me H    H                                                   4-Cl H    H    Me Me H    H                                                   4-Br H    H    Me Me H    H                                                   4-OCF.sub.3                                                                        H    H    Me Me H    H                                                   4-CF.sub.3                                                                         H    CO.sub.2 Me                                                                        Me Me H    H                                                   4-Cl H    CO.sub.2 Me                                                                        Me Me H    H                                                   4-Br H    CO.sub.2 Me                                                                        Me Me H    H                                                   4-OCF.sub.3                                                                        H    CO.sub.2 Me                                                                        Me Me H    H                                                   4-CF.sub.3                                                                         5-OCF.sub.2 H                                                                      H    Me Me H    H                                                   4-Cl 5-OCF.sub.2 H                                                                      H    Me Me H    H                                                   4-Br 5-OCF.sub.2 H                                                                      H    Me Me H    H                                                   4-OCF.sub.3                                                                        5-OCF.sub.2 H                                                                      H    Me Me H    H                                                   4-CF.sub.3                                                                         5-OCF.sub.2 H                                                                      CO.sub.2 Me                                                                        Me Me H    H                                                   4-Cl 5-OCF.sub.2 H                                                                      CO.sub.2 Me                                                                        Me Me H    H                                                   4-Br 5-OCF.sub.2 H                                                                      CO.sub.2 Me                                                                        Me Me H    H                                                   4-OCF.sub.3                                                                        5-OCF.sub. 2 H                                                                     CO.sub.2 Me                                                                        Me Me H    H                                                   4-CF.sub.3                                                                         5-Cl H    Me Me H    H                                                   4-Cl 5-Cl H    Me Me H    H                                                   4-Br 5-Cl H    Me Me H    H                                                   4-OCF.sub.3                                                                        5-Cl H    Me Me H    H                                                   4-CF.sub.3                                                                         5-Cl CO.sub.2 Me                                                                        Me Me H    H                                                   4-Cl 5-Cl CO.sub.2 Me                                                                        Me Me H    H                                                   4-Br 5-Cl CO.sub.2 Me                                                                        Me Me H    H                                                   4-OCF.sub.3                                                                        5-Cl CO.sub.2 Me                                                                        Me Me H    H                                                   4-CF.sub.3                                                                         H    H    H  Me H    H                                                   4-Cl H    H    H  Me H    H                                                   4-CF.sub.3                                                                         H    CO.sub.2 Me                                                                        H  Me H    H                                                   4-Cl H    CO.sub.2 Me                                                                        H  Me H    H                                                   4-CF.sub.3                                                                         5-Cl H    H  Me H    H                                                   4-Cl 5-Cl H    H  Me H    H                                                   4-CF.sub.3                                                                         5-Cl CO.sub.2 Me                                                                        H  Me H    H                                                   4-Cl 5-Cl CO.sub.2 Me                                                                        H  Me H    H                                                   4-CF.sub.3                                                                         H    H    H  H  Me   H                                                   4-Cl H    H    H  H  Me   H                                                   4-CF.sub.3                                                                         H    CO.sub.2 Me                                                                        H  H  Me   H                                                   4-Cl H    CO.sub.2 Me                                                                        H  H  Me   H                                                   4-CF.sub.3                                                                         5-Cl H    H  H  Me   H                                                   4-Cl 5-Cl H    H  H  Me   H                                                   4-CF.sub.3                                                                         5-Cl CO.sub.2 Me                                                                        H  H  Me   H                                                   4-Cl 5-Cl CO.sub.2 Me                                                                        H  H  Me   H                                                   4-CF.sub.3                                                                         H    H    H  H  H    Me                                                  4-Cl H    H    H  H  H    Me                                                  4-CF.sub.3                                                                         H    CO.sub.2 Me                                                                        H  H  H    Me                                                  4-Cl H    CO.sub.2 Me                                                                        H  H  H    Me                                                  4-CF.sub.3                                                                         5-Cl H    H  H  H    Me                                                  4-Cl 5-Cl H    H  H  H    Me                                                  4-CF.sub.3                                                                         5-Cl CO.sub.2 Me                                                                        H  H  H    Me                                                  4-Cl 5-Cl CO.sub.2 Me                                                                        H  H  H    Me                                                  CF.sub.3                                                                           H    H    H  H  Me   Me                                                  Cl   H    H    H  H  Me   Me                                                  Br   H    H    H  H  Me   Me                                                  CF.sub.3                                                                           H    CO.sub.2 Me                                                                        H  H  Me   Me                                                  Cl   H    CO.sub.2 Me                                                                        H  H  Me   Me                                                  Br   H    CO.sub.2 Me                                                                        H  H  Me   Me                                                  CF.sub.3                                                                           5-Cl H    H  H  Me   Me                                                  Cl   5-Cl H    H  H  Me   Me                                                  Br   5-Cl H    H  H  Me   Me                                                  CF.sub.3                                                                           5-Cl CO.sub.2 Me                                                                        H  H  Me   Me                                                  Cl   5-Cl CO.sub.2 Me                                                                        H  H  Me   Me                                                  Br   5-Cl CO.sub.2 Me                                                                        H  H  Me   Me                                                  CF.sub.3                                                                           5-OCF.sub.2 H                                                                      H    H  H  Me   Me                                                  Cl   5-OCF.sub.2 H                                                                      H    H  H  Me   Me                                                  Br   5-OCF.sub.2 H                                                                      H    H  H  Me   Me                                                  CF.sub.3                                                                           5-OCF.sub.2 H                                                                      CO.sub.2 Me                                                                        H  H  Me   Me                                                  Cl   5-OCF.sub.2 H                                                                      CO.sub.2 Me                                                                        H  H  Me   Me                                                  Br   5-OCF.sub.2 H                                                                      CO.sub.2 Me                                                                        H  H  Me   Me                                                  CF.sub.3                                                                           4-F  H    H  H  Me   Me                                                  Cl   4-F  H    H  H  Me   Me                                                  Br   4-F  H    H  H  Me   Me                                                  CF.sub.3                                                                           4-F  CO.sub.2 Me                                                                        H  H  Me   Me                                                  Cl   4-F  CO.sub.2 Me                                                                        H  H  Me   Me                                                  Br   4-F  CO.sub.2 Me                                                                        H  H  Me   Me                                                  4-CF.sub.3                                                                         H    CO.sub.2 Me                                                                        i-Pr                                                                             H  H    H                                                   4-CF.sub.3                                                                         H    CO.sub.2 Me                                                                        H  i-Pr                                                                             H    H                                                   4-CF.sub.3                                                                         H    CO.sub.2 Me                                                                        H  H  Ph   H                                                   4-CF.sub.3                                                                         H    CO.sub.2 Me                                                                        H  H  H    Ph                                                  4-CF.sub.3                                                                         5-Cl CO.sub.2 Me                                                                        Cl H  H    H                                                   4-CF.sub.3                                                                         5-Cl CO.sub.2 Me                                                                        H  Cl H    H                                                   4-CF.sub.3                                                                         5-Cl CO.sub.2 Me                                                                        F  H  H    H                                                   4-CF.sub.3                                                                         5-Cl CO.sub.2 Me                                                                        H  F  H    H                                                   4-CF.sub.3                                                                         5-F  CO.sub.2 Me                                                                        H  H  CO.sub.2 Me                                                                        H                                                   4-CF.sub.3                                                                         5-F  CO.sub.2 Me                                                                        H  H  H    CO.sub.2 Me                                         4-CF.sub.3                                                                         5-F  CO.sub.2 Me                                                                        Et H  H    H                                                   4-CF.sub.3                                                                         5-F  CO.sub.2 Me                                                                        H  Et H    H                                                   4-CF.sub.3                                                                         5-OCF.sub.2 H                                                                      CO.sub.2 Me                                                                        Ph H  H    H                                                   4-CF.sub.3                                                                         5-OCF.sub.2 H                                                                      CO.sub.2 Me                                                                        H  Ph H    H                                                   4-CF.sub.3                                                                         5-OCF.sub.2 H                                                                      CO.sub.2 Me                                                                        H  Me Me   H                                                   4-CF.sub.3                                                                         5-OCF.sub.2 H                                                                      CO.sub.2 Me                                                                        Me H  H    Me                                                  4-CF.sub.3                                                                         4-Cl CO.sub.2 Me                                                                        i-Pr                                                                             H  H    H                                                   4-CF.sub.3                                                                         4-Cl CO.sub.2 Me                                                                        H  i-Pr                                                                             H    H                                                   4-CF.sub.3                                                                         4-Cl CO.sub.2 Me                                                                        Et Et H    H                                                   4-CF.sub.3                                                                         4-Cl CO.sub.2 Me                                                                        Et Me H    H                                                   4-CF.sub.3                                                                         4-F  CO.sub.2 Me                                                                        Br H  H    H                                                   4-CF.sub.3                                                                         4-F  CO.sub.2 Me                                                                        H  Br H    H                                                   4-CF.sub.3                                                                         4-F  CO.sub.2 Me                                                                        i-Pr                                                                             H  H    H                                                   4-CF.sub.3                                                                         4-F  CO.sub.2 Me                                                                        H  i-Pr                                                                             H    H                                                   __________________________________________________________________________

                  TABLE 17                                                        ______________________________________                                                                                  Phys.                                                                         Prop.                               R.sub.1                                                                              R.sub.2 B      V     R.sub.8.sup.a                                                                        R.sub.8.sup.b                                                                        (m.p. °C.)                   ______________________________________                                        4-CF.sub.3                                                                           H       H      O     Me     H                                          4-Cl   H       H      O     Me     H                                          4-Br   H       H      O     Me     H                                          4-OCF.sub.2 H                                                                        H       H      O     Me     H                                          4-CF.sub.3                                                                           H       H      O     H      Me                                         4-Cl   H       H      O     H      Me                                         4-Br   H       H      O     H      Me                                         4-OCF.sub.2 H                                                                        H       H      O     H      Me                                         4-CF.sub.3                                                                           H       H      O     Me     Me                                         4-Cl   H       H      O     Me     Me                                         4-Br   H       H      O     Me     Me                                         4-OCF.sub.2 H                                                                        H       H      O     Me     Me                                         4-CF.sub.3                                                                           H       H      O     Ph     H                                          4-Cl   H       H      O     Ph     H                                          4-Br   H       H      O     Ph     H                                          4-OCF.sub.2 H                                                                        H       H      O     Ph     H                                          4-CF.sub.3                                                                           H       H      O     H      Ph                                         4-Cl   H       H      O     H      Ph                                         4-Br   H       H      O     H      Ph                                         4-OCF.sub.2 H                                                                        H       H      O     H      Ph                                         4-CF.sub.3                                                                           H       H      O     CO.sub.2 Me                                                                          H                                          4-Cl   H       H      O     CO.sub.2 Me                                                                          H                                          4-Br   H       H      O     H      CO.sub.2 Me                                4-OCF.sub.2 H                                                                        H       H      O     H      CO.sub.2 Me                                4-CF.sub.3                                                                           5-Cl    H      O     Me     H                                          4-Cl   5-Cl    H      O     Me     H                                          4-Br   5-Cl    H      O     Me     H                                          4-OCF.sub.2 H                                                                        5-Cl    H      O     Me     H                                          4-CF.sub.3                                                                           5-Cl    H      O     H      Me                                         4-Cl   5-Cl    H      O     H      Me                                         4-Br   5-Cl    H      O     H      Me                                         4-OCF.sub.2 H                                                                        5-Cl    H      O     H      Me                                         4-CF.sub.3                                                                           5-Cl    H      O     Me     Me                                         4-Cl   5-Cl    H      O     Me     Me                                         4-Br   5-Cl    H      O     Me     Me                                         4-OCF.sub.2 H                                                                        5-Cl    H      O     Me     Me                                         4-CF.sub.3                                                                           5-Cl    H      O     Ph     H                                          4-Cl   5-Cl    H      O     Ph     H                                          4-Br   5-Cl    H      O     Ph     H                                          4-OCF.sub.2 H                                                                        5-Cl    H      O     Ph     H                                          4-CF.sub.3                                                                           5-Cl    H      O     H      Ph                                         4-Cl   5-Cl    H      O     H      Ph                                         4-Br   5-Cl    H      O     H      Ph                                         4-OCF.sub.2 H                                                                        5-Cl    H      O     H      Ph                                         4-CF.sub.3                                                                           5-Cl    H      O     CO.sub.2 Me                                                                          H                                          4-Cl   5-Cl    H      O     CO.sub.2 Me                                                                          H                                          4-Br   5-Cl    H      O     H      CO.sub.2 Me                                4-OCF.sub.2 H                                                                        5-Cl    H      O     H      CO.sub.2 Me                                4-CF.sub.3                                                                           H       H      S     Me     H      208 to 210                          4-Cl   H       H      S     Me     H      172 to 178                          4-Br   H       H      S     Me     H      185 to 187                          4-OCF.sub.2 H                                                                        H       H      S     Me     H                                          4-CF.sub.3                                                                           H       H      S     H      Me     168 to 170                          4-Cl   H       H      S     H      Me     155 to 156                          4-Br   H       H      S     H      Me     172 to 180                          4-OCF.sub.2 H                                                                        H       H      S     H      Me                                         4-CF.sub.3                                                                           H       H      S     Me     Me     183 to 184                          4-Cl   H       H      S     Me     Me     181 to 186                          4-Br   H       H      S     Me     Me     182 to 185                          4-OCF.sub.2 H                                                                        H       H      S     Me     Me                                         4-CF.sub.3                                                                           H       H      S     Ph     H                                          4-Cl   H       H      S     Ph     H                                          4-Br   H       H      S     Ph     H                                          4-OCF.sub.2 H                                                                        H       H      S     Ph     H                                          4-CF.sub.3                                                                           H       H      S     H      Ph                                         4-Cl   H       H      S     H      Ph                                         4-Br   H       H      S     H      Ph                                         4-OCF.sub.2 H                                                                        H       H      S     H      Ph                                         4-CF.sub.3                                                                           H       H      S     CO.sub.2 Me                                                                          H                                          4-Cl   H       H      S     CO.sub.2 Me                                                                          H                                          4-Br   H       H      S     H      CO.sub.2 Me                                4-OCF.sub.2 H                                                                        H       H      S     H      CO.sub.2 Me                                4-CF.sub.3                                                                           5-Cl    H      S     Me     H      251 to 255                          4-Cl   5-Cl    H      S     Me     H      222 to 226                          4-Br   5-Cl    H      S     Me     H      228 to 230                          4-OCF.sub.2 H                                                                        5-Cl    H      S     Me     H                                          4-CF.sub.3                                                                           5-Cl    H      S     H      Me     171 to 173                          4-Cl   5-Cl    H      S     H      Me     170 to 176                          4-Br   5-Cl    H      S     H      Me     120 to 125                          4-OCF.sub.2 H                                                                        5-Cl    H      S     H      Me                                         4-CF.sub.3                                                                           5-Cl    H      S     Me     Me     200 to 202                          4-Cl   5-Cl    H      S     Me     Me     190 to 193                          4-Br   5-Cl    H      S     Me     Me     204 to 207                          4-OCF.sub.2 H                                                                        5-Cl    H      S     Me     Me                                         4-CF.sub.3                                                                           5-Cl    H      S     Ph     H                                          4-Cl   5-Cl    H      S     Ph     H                                          4-Br   5-Cl    H      S     Ph     H                                          4-OCF.sub.2 H                                                                        5-Cl    H      S     Ph     H                                          4-CF.sub.3                                                                           5-Cl    H      S     H      PH                                         4-Cl   5-Cl    H      S     H      Ph                                         4-Br   5-Cl    H      S     H      Ph                                         4-OCF.sub.2 H                                                                        5-Cl    H      S     H      Ph                                         4-CF.sub.3                                                                           5-Cl    H      S     CO.sub.2 Me                                                                          H                                          4-Cl   5-Cl    H      S     CO.sub.2 Me                                                                          H                                          4-Br   5-Cl    H      S     H      CO.sub.2 Me                                4-OCF.sub.2 H                                                                        5-Cl    H      S     H      CO.sub.2 Me                                4-CF.sub.3                                                                           5-Br    H      S     Me     H                                          4-Cl   5-Br    H      S     Me     H                                          4-Br   5-Br    H      S     Me     H                                          4-CF.sub.3                                                                           5-F     H      S     Me     H                                          4-Cl   5-F     H      S     Me     H                                          4-Br   5-F     H      S     Me     H                                          4-CF.sub.3                                                                           4-F     H      S     Me     H                                          4-Cl   4-F     H      S     Me     H                                          4-Br   4-F     H      S     Me     H                                          4-CF.sub.3                                                                           5-Br    H      S     H      Me                                         4-Cl   5-Br    H      S     H      Me                                         4-Br   5-Br    H      S     H      Me                                         4-CF.sub.3                                                                           5-F     H      S     H      Me                                         4-Cl   5-F     H      S     H      Me                                         4-Br   5-F     H      S     H      Me                                         4-CF.sub.3                                                                           4-F     H      S     H      Me                                         4-Cl   4-F     H      S     H      Me                                         4-Br   4-F     H      S     H      Me                                         4-CF.sub.3                                                                           5-Br    H      S     Me     Me     190 to 196                          4-Cl   5-Br    H      S     Me     Me     165 to 186                          4-Br   5-Br    H      S     Me     Me     208 to 211                          4-CF.sub.3                                                                           5-F     H      S     Me     Me                                         4-Cl   5-F     H      S     Me     Me                                         4-Br   5-F     H      S     Me     Me                                         4-CF.sub.3                                                                           4-F     H      S     Me     Me                                         4-Cl   4-F     H      S     Me     Me                                         4-Br   4-F     H      S     Me     Me                                         4-CF.sub.3                                                                           4-Cl    H      S     Me     Me     170 to 173                          4-Cl   4-Cl    H      S     Me     Me     150 to 168                          4-Br   4-Cl    H      S     Me     Me     158 to 170                          ______________________________________                                    

                  TABLE 18                                                        ______________________________________                                                                              Phys.                                   R.sub.1                                                                             R.sub.2  B        V   R.sub.8.sup.a                                                                      R.sub.8.sup.b                                                                      Prop. (m.p. °C.)                 ______________________________________                                        4-CF.sub.3                                                                          H        H        O   Me   H                                            4-CF.sub.3                                                                          H        CO.sub.2 Me                                                                            O   Me   H                                            4-CF.sub.3                                                                          5-Cl     H        S   Me   H                                            4-CF.sub.3                                                                          5-Cl     CO.sub.2 Me                                                                            S   H    Me                                           4-CF.sub.3                                                                          5-Cl     H        O   H    Me                                           4-CF.sub.3                                                                          5-Cl     CO.sub.2 Me                                                                            O   H    Me                                           4-CF.sub.3                                                                          5-F      H        S   Me   Me                                           4-CF.sub.3                                                                          5-F      CO.sub.2 Me                                                                            S   Me   Me                                           4-CF.sub.3                                                                          5-OCF.sub.2 H                                                                          H        O   Me   Me                                           4-CF.sub.3                                                                          5-OCF.sub.2 H                                                                          CO.sub.2 Me                                                                            O   H    Me                                           4-CF.sub.3                                                                          4-Cl     H        S   H    Me                                           4-CF.sub.3                                                                          4-Cl     CO.sub.2 Me                                                                            S   H    Me                                           4-Cl  H        H        O   Me   Me                                           4-Cl  H        CO.sub.2 Me                                                                            O   Me   Me                                           4-Cl  5-Cl     H        S   Me   Me                                           4-Cl  5-Cl     CO.sub.2 Me                                                                            S   H    Me                                           4-Cl  5-Cl     H        O   H    Me                                           4-Cl  5-Cl     CO.sub.2 Me                                                                            O   H    Me                                           4-Cl  5-OCF.sub.2 H                                                                          H        S   Me   Me                                           4-Cl  5-OCF.sub.2 H                                                                          CO.sub.2 Me                                                                            S   Me   Me                                           4-Cl  5-OCF.sub.2 H                                                                          H        O   Me   Me                                           4-Cl  5-OCF.sub.2 H                                                                          CO.sub.2 Me                                                                            O   H    Me                                           4-Cl  4-F      H        S   H    Me                                           4-Cl  4-F      CO.sub.2 Me                                                                            S   H    Me                                           ______________________________________                                    

Formulation and Use

The compounds of this invention will generally be used in formulationwith an agriculturally suitable carrier comprising a liquid or soliddiluent or an organic solvent. Useful formulations of the compounds ofFormula I can be prepared in conventional ways. They include dusts,granules, pellets, solutions, suspensions, emulsions, wettable powders,emulsifiable concentrates, dry flowables and the like. Many of these canbe applied directly. Sprayable formulations can be extended in suitablemedia and used at spray volumes of from about one to several hundredliters per hectare. High strength compositions are primarily used asintermediates for further formulation. The formulations, broadly,contain about 1% to 99% by weight of active ingredient(s) and at leastone of (a) about 0.1% to 20% surfactant(s) and (b) about 5% to 99% solidor liquid diluent(s). More specifically, they will contain effectiveamounts of these ingredients in the following approximate proportions:

    ______________________________________                                                    Active  Percent by Weight                                                     Ingredient                                                                            Diluent (s)                                                                             Surfactant (s)                                  ______________________________________                                        Wettable Powders                                                                            25-90     0-74      1-10                                        Oil Suspensions,                                                                            5-50      40-95     0-15                                        Emulsions, Solutions,                                                         (including Emulsifiable                                                       Concentrates)                                                                 Dusts         1-25      70-99     0-5                                         Granules and Pellets                                                                        1-95      5-99      0-15                                        High Strength 90-99     0-10      0-2                                         Compositions                                                                  ______________________________________                                    

Lower or higher levels of active ingredient can, of course, be presentdepending on the intended use and the physical properties of thecompound. Higher ratios of surfactant to active ingredient are sometimesdesirable, and are achieved by incorporation into the formulation or byrank mixing.

Typical solid diluents are described in Watkins, et al., "Handbook ofInsecticide Dust Diluents and Carriers", 2nd Ed., Dorland Books,Caldwell, New Jersey. The more absorptive diluents are preferred forwettable powders and the denser ones for dusts. Typical liquid diluentsand solvents are described in Marsden, "Solvents Guide," 2nd Ed.,Interscience, New York, 1950. Solubility under 0.1% is preferred forsuspension concentrates; solution concentrates are preferably stableagainst phase separation at 0° C. "McCutcheon's Detergents andEmulsifiers Annual", Allured Publ. Corp., Ridgewood, New Jersey, as wellas Sisely and Wood, "Encyclopedia of Surface Active Agents", ChemicalPubl. Co., Inc., New York, 1964, list surfactants and recommended uses.All formulations can contain minor amounts of additives to reduce foam,caking, corrosion, microbiological growth, etc. Preferably, ingredientsshould be approved by the U.S. Environmental Protection Agency for theuse intended.

The methods of making such compositions are well known. Solutions areprepared by simply mixing the ingredients. Fine solid compositions aremade by blending and, usually, grinding as in a hammer or fluid energymill. Suspensions are prepared by wet milling (see, for example,Littler, U.S. Pat. No. 3,060,084). Granules and pellets may be made byspraying the active material upon preformed granular carriers or byagglomeration techniques. See J. E. Browning, "Agglomeration", ChemicalEngineering, Dec. 4, 1967, pages 147 and following, and "Perry'sChemical Engineer's Handbook", 4th Ed., McGraw-Hill, New York, 1963,pages 8 to 59 and following.

Examples of useful formulations of compounds of the present inventionare as follows:

EXAMPLE A Emulsifiable Concentrate

    ______________________________________                                        3,3a,4,5-tetrahydro-3a-methyl-N-[4-(triflluoromethyl)-                                                       5%                                             phenyl]-2H-benz[g]indazole-2-carboxamide                                      blend of oil soluble sulfonates                                                                              4%                                             and polyoxyethylene ethers                                                    xylene                        91%                                             ______________________________________                                    

The ingredients are combined and stirred with gentle warming to speedsolution. A fine screen filter is included in packaging operation toinsure the absence of any extraneous undissolved material in theproduct.

EXAMPLE B Wettable Powder

    ______________________________________                                        Methyl 3,3a,4,5-tetrahydro-2-[[4-(trifluoromethyl)-                                                       30%                                               phenylamino]carbonyl]-2H-benz[ g]indazole-3a-                                 carboxylate                                                                   sodium alkylnaphthalenesulfonate                                                                          2%                                                sodium ligninsulfonate      2%                                                synthetic amorphous silica  3%                                                kaolinite                   63%                                               ______________________________________                                    

The active ingredient, warmed to reduce viscosity, is sprayed onto theinert materials in a blender. After grinding in a hammer-mill, thematerial is reblended and sifted through a 50 mesh screen.

EXAMPLE C Dust

    ______________________________________                                        Wettable powder of Example B                                                                       10%                                                      pyrophyllite (powder)                                                                              90%                                                      ______________________________________                                    

The wettable powder and the pyrophyllite diluent are thoroughly blendedand then packaged. The product is suitable for use as a dust.

EXAMPLE D Granule

    ______________________________________                                        3,3a,4,5-tetrahydro-3a-methyl-N-[4-(trifluoromethyl)-                                                      10%                                              phenyl]-2H-benz[g]indazole-2-carboxamide                                      attapulgite granules (low volative                                                                         90%                                              matter, 0.71/0.30 mm; U.S.S. No.                                              25-50 sieves)                                                                 ______________________________________                                    

The active ingredient is dissolved in a suitable solvent and sprayedonto dedusted attapulgite granules in a double cone blender. Thegranules are warmed to drive off solvent, cooled and packaged.

EXAMPLE E Granule

    ______________________________________                                        Wettable powder of Example D                                                                        15%                                                     gypsum                69%                                                     potassium sulfate     16%                                                     ______________________________________                                    

The ingredients are blended in a rotating mixer and water sprayed on toaccomplish granulation. When most of the material has reached thedesired range of 0.1 to 0.42 mm (U.S.S. No. 18 to 40 sieves), thegranules are removed, dried, and screened. Oversize material is crushedto produce additional material in the desired range. These granulescontain 4.5% active ingredient.

EXAMPLE F Solution

    ______________________________________                                        Methyl 3,3a,4,5-tetrahydro-2-[[4-(trifluoromethyl)-                                                       10%                                               phenylamino]carbonyl]-2H-benz[g]indazole-3a-                                  carboxylate                                                                   isophrone                   90%                                               ______________________________________                                    

The ingredients are combined and stirred to produce a solution suitablefor direct, low volume application.

Compounds of Formula I can also be mixed with one or more otherinsecticides, fungicides, nematocides, bactericides, acaricides, orother biologically active compounds to form a multi-component pesticidegiving an even broader spectrum of effective agricultural protection.Examples of other agricultural protectants with which compounds of thepresent invention can be mixed or formulated are:

Insecticides:

3-hydroxy-N-methylcrotonamide(dimethylphosphate)ester (monocrotophos)

methylcarbamic acid, ester with 2,3-dihydro-2,2dimethyl-7-benzofuranol(carbofuran)

O-[2,4,5-trichloro-α-(chloromethyl)benzyl]phosphoric acid, O',O'-dimethyl ester (tetrachlorvinphos)

2-mercaptosuccinic acid, diethyl ester, S-ester with thionophosphoricacid, dimethyl ester (malathion)

phosphorothioic acid, O,O-dimethyl, O-p-nitrophenyl ester (methylparathion)

methylcarbamic acid, ester with α-naphthol (carbaryl) methylO-(methylcarbamoyl)thiolacetohydroxamate (methomyl)

N'-(4-chloro-o-tolyl)-N,N-dimethylformamidine (chlordimeform)

O,O-diethyl-O-(2-isopropyl-4-methyl-6-pyrimidylphosphorothioate(diazinon)

octachlorocamphene (toxaphene)

O-ethyl O-p-nitrophenyl phenylphosphonothioate (EPN)

(S)-α-cyano-m-phenoxybenzyl(1R,3R)-3-(2,2-dibromovinyl)-2,2-dimethylcyclopropanecarboxylate(deltamethrin)

Methyl N',N'-dimethyl-N-[(methylcarbamoyl)oxy]-1-thiooxamimidate(oxamyl)

cyano(3-phenoxyphenyl)-methyl-4-chloro-α-(1-methylethyl)benzeneacetate(fenvalerate)

(3-phenoxyphenyl)methyl(+)-cis,trans-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate(permethrin)

α-cyano-3-phenoxybenzyl 3-(2,2-dichlorovinyl)-2,2dimethylcyclopropanecarboxylate (cypermethrin)

O-ethyl-S-(p-chlorophenyl)ethylphosphonodithioate (profenofos)

phosphorothiolothionic acid, O-ethyl-O-[4-(methylthio)phenyl]-S-n-propylester (sulprofos).

Additional insecticides are listed hereafter by their common names:triflumuron, diflubenzuron, methoprene, buprofezin, thiodicarb,acephate, azinphos-methyl, chlorpyrifos, dimethoate, fonophos,isofenphos, methidathion, methamidiphos, monocrotophos, phosmet,phosphamidon, phosalone, pirimicarb, phorate, profenofos, terbufos,trichlorfon, methoxychlor bifenthrin, biphenate, cyfluthrin,fenpropathrin, fluvalinate, flucythrinate, tralomethrin, metaldehyde androtenone.

Fungicides:

methyl 2-benzimidazolecarbamate (carbendazim)

tetramethylthiuram disulfide (thiuram)

n-dodecylguanidine acetate (dodine)

manganese ethylenebisdithiocarbamate (maneb)

1,4-dichloro-2,5-dimethoxybenzene (chloroneb)

methyl 1-(butylcarbamoyl)-2-benzimidazolecarbamate (benomyl)

1-[2-(2,4-dichlorophenyl)-4-propyl-1,3-dioxolan-2ylmethyl]-1H-1,2,4-triazole(propiconazole)

2-cyano-N-ethylcarbamoyl-2-methoxyiminoacetamide (cymoxanil)

1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol1-yl)-2-butanone(triadimefon)

N-(trichloromethylthio)tetrahydrophthalimide (captan)

N-(trichloromethylthio)phthalimide (folpet)

1-[[[bis(4-fluorophenyl)][methyl]silyl)methyl]-1H1,2,4-triazole.

Nematocides:

S-methyl 1-(dimethylcarbamoyl)-N-(methylcarbamoyloxy)thioformimidate

S-methyl 1-carbamoyl-N-(methylcarbamoyloxy)thioformimidate

N-isopropylphosphoramidic acid, O-ethylO''-[4-(methylthio)-m-tolyl]diester (fenamiphos).

Bactericides:

tribasic copper sulfate

streptomycin sulfate.

Acaricides:

senecioic acid, ester with 2-sec-butyl-4,6-dinitrophenol (binapacryl)

6-methyl-1,3-dithiolo[4,5-β]quinoxalin-2-one (oxythioquinox)

ethyl 4,4'-dichlorobenzilate (chlorobenzilate)

1,1-bis(p-chlorophenyl)-2,2,2-trichlcroethanol (dicoiol)

bis(pentachloro-2,4-cyclopentadien-1-yl) (dienochlor)

tricyclohexyltin hydroxide (cyhexatin)

trans-5-(4-chlorophenyl)-N-cyclohexyl-4-methyl-2-oxothiazolidine-3-carboxamide(hexythiazox)

amitraz

propargite

fenbutatin-oxide

bisclofentezin.

Biological

Bacillus t huringiensis

Avermectin B.

Utility

The compounds of the present invention exhibit activity against a widespectrum of foliar and soil inhabiting insects. Those skilled in the artwill recognize that not all compounds are equally effective against allinsects, but compounds of this invention display control of many of theeconomically important pest species of the insect orders Lepidoptera,Homoptera, and Coleoptera among many others. The specific species forwhich control is exemplified below are: fall armyworm, Spodopterafrugiperda; boll weevil, Anthonomus grandis; European corn borer,Ostrinia nubilalis; southern corn rootworm, Diabrotica undecimpunctatahowardi; aster leafhopper, Macrosteles fascifrons; Tobacco budworm,Heliothis virescens. The pest control afforded by the compounds of thepresent invention is not limited, however, to these species.

Application

Insects are controlled and agricultural crops are protected by applyingone or more of the Formula I compounds of this invention, in aneffective amount, to the locus of infestation, to the area to beprotected, or directly on the pests to be controlled. A preferred methodof application is by spraying with spray equipment that distributes thecompound on the foliage, in the soil, or to the plant part that isinfested or needs to be protected. Alternatively, granular formulationsof these compounds can be applied to soil or foliage or, optionally,incorporated into the soil. Either aerial or ground application can beused.

The substituted indazole(s) of this invention can be applied inits(their) pure state, but most often application will be of aformulation comprising one or more compounds of this invention, in anagriculturally suitable carrier or diluent. A most preferred method ofapplication involves spraying a water dispersion or refined oil solutionof the compounds.

The rate of application of the Formula I compounds required foreffective control will depend on such factors as the species of insectto be controlled, the pest's life stage, its size, its location, thehost crop, time of year of application, ambient moisture, temperatureconditions, and the like. In general, application rates of 0.05 to 2 kgof active ingredient per hectare are sufficient to provide effectivecontrol in large scale field operations under normal circumstances, butas little as 0.01 kg/hectare may be sufficient or as much as 8kg/hectare may be required, depending upon the factors listed above.

The following Examples demonstrate the control efficacy of compounds ofFormula I on specific insect pests wherein Compounds 1 through 8 arethose of Examples I to B and Compounds 9 through 181 are as depicted inTables 19 and 20. Compounds not listed were either not tested or did noteffect at least 80% mortality in that screen.

                                      TABLE 19                                    __________________________________________________________________________     ##STR22##                                                                    CMPD R.sub.1                                                                             R.sub.2                                                                             J     Y     t  B                                             __________________________________________________________________________     9   4-Cl  H     H     H     1  H                                             10   4-Br  H     H     H     1  H                                             11   4-OCF.sub.3                                                                         H     H     H     1  H                                             12   4-Cl  5-Cl  H     H     1  H                                             13   4-Br  5-Cl  H     H     1  H                                             14   4-CF.sub.3                                                                          5-OMe H     H     1  H                                             15   4-CF.sub.3                                                                          5-OCF.sub.2 H                                                                       H     H     1  H                                             16   4-CF.sub.3                                                                          5-F   H     H     1  H                                             17   4-CF.sub.3                                                                          4-Cl  H     H     1  H                                             18   4-CF.sub.3                                                                          4-F   H     H     1  H                                             19   4-CF.sub.3                                                                          5,6-di-Cl                                                                           H     H     1  H                                             20   4-CF.sub.3                                                                          5-F   H     H     1  CO.sub.2 Me                                   21   4-CF.sub.3                                                                          5-OMe H     H     1  CO.sub.2 Me                                   22   4-CF.sub.3                                                                          4-Cl  H     H     1  CO.sub.2 Me                                   23   4-CF.sub.3                                                                          4-F   H     H     1  CO.sub.2 Me                                   24   4-CF.sub.3                                                                          5,6-di-Cl                                                                           H     H     1  CO.sub.2 Me                                   25   4-CF.sub.3                                                                          H     H     H     1  Et                                            26   4-CF.sub.3                                                                          H     H     H     1  CH.sub.2Ph-4-F                                27   4-CF.sub.3                                                                          H     H     H     1  (CH.sub.2).sub.2 CN                           28   4-CF.sub.3                                                                          H     H     H     1  (CH.sub.2).sub.3 CN                           29   4-CF.sub.3                                                                          H     H     H     1  CO.sub.2 Et                                   30   4-CF.sub.3                                                                          H     H     H     1  CO.sub.2 (CH.sub.2).sub.2 Cl                  31   4-CF.sub.3                                                                          H     H     H     1  CO.sub.2 (CH.sub.2).sub.2 Br                  32   4-CF.sub.3                                                                          H     H     H     1  CO.sub.2 CH.sub.2 CF.sub.3                    33   4-CF.sub.3                                                                          H     H     H     1  CO.sub.2 CH.sub.2 CCl.sub.3                   34   4-CF.sub.3                                                                          H     H     H     1  CONH.sub.2                                    35   4-CF.sub.3                                                                          H     H     H     1  CONHMe                                        36   4-CF.sub.3                                                                          H     H     H     1  CONMe.sub.2                                   37   4-CF.sub.3                                                                          H     H     H     1  COH(H)CH.sub.2 CHCH.sub. 2                    38   4-CF.sub.3                                                                          H     H     H     1  CON(Me)CH.sub.2 CHCH.sub.2                    39   4-CF.sub.3                                                                          H     H     H     1  CONH(4-ClPh)                                  40   4-Cl  5-Cl  H     H     1  CO.sub.2 Me                                   41   4-Br  5-Cl  H     H     1  CO.sub.2 Me                                   42   4-CF.sub.3                                                                          H     H     H     1  CO-piperidinyl                                43   4-CF.sub.3                                                                          H     H     H     1  CO.sub.2 H                                    44   4-CF.sub.3                                                                          H     H     H     1  CO.sub.2 Na                                   45   4-CF.sub.3                                                                          H     H     C(O)Me                                                                              1  CO.sub.2 Me                                   46   4-CF.sub.3                                                                          H     H     Me    1  CO.sub.2 Me                                   47   4-CF.sub.3                                                                          H     H     CO.sub.2 Me                                                                         1  CO.sub.2 Me                                   48   4-CF.sub.3                                                                          H     H     C(O)Me                                                                              1  H                                             49   4-CF.sub.3                                                                          H     4-FPh H     1  H                                             50   4-Cl  H     4-FPh H     1  H                                             51   4-CF.sub.3                                                                          H     4-ClPh                                                                              H     1  H                                             52   4-Cl  H     4-ClPh                                                                              H     1  H                                             53   4-CF.sub.3                                                                          H     H     H     1  CH.sub.2 CHCH.sub.2                           54   4-CF.sub.3                                                                          H     H     H     1  CH.sub.2 Ph                                   55   4-CF.sub.3                                                                          H     H     H     1  CO.sub.2 Et                                   56   4-Cl  H     H     H     1  CO.sub.2 Et                                   57   4-Br  H     H     H     1  CO.sub.2 Me                                   58   4-Br  H     H     H     1  CO.sub.2 Et                                   59   4-Cl  H     H     H     1  CO.sub.2 Me                                   60   4-Cl  5-OMe H     H     1  H                                             61   4-CF.sub.3                                                                          H     H     H     1  CO.sub.2 Ph                                   62   4-CF.sub.3                                                                          H     H     CO.sub.2 -t-Bu                                                                      1  H                                             63   4-SMe 5-Cl  H     H     1  H                                             64   4-CO.sub.2 Et                                                                       5-Cl  H     H     1  H                                             65   4-SMe 5-Cl  H     H     1  CO.sub.2 Me                                   66   4-CO.sub.2 Et                                                                       5-Cl  H     H     1  CO.sub.2 Me                                   67   4-CF.sub.3                                                                          H     H     H     2  H                                             68   4-CF.sub.3                                                                          H     H     H     2  Me                                            69   4-Cl  H     H     H     2  H                                             70   4-Cl  H     H     H     2  Me                                            __________________________________________________________________________

                  TABLE 20                                                        ______________________________________                                         ##STR23##                                                                    CMPD  R.sub.1  R.sub.2 Y      V      R.sub.8.sup.a                                                                       R.sub.8.sup.b                      ______________________________________                                        71    4-CF.sub.3                                                                             H       H      O      H     H                                  72    4-CF.sub.3                                                                             H       H      S      H     H                                  73    3,4-di-Cl                                                                              H       H      O      H     H                                  74    4-Br     H       H      O      H     H                                  75    3-CF.sub.3                                                                             H       H      O      H     H                                  76    4-Cl     H       H      O      H     H                                  77    3-Cl     H       H      O      H     H                                  78    3,4-di-Cl                                                                              H       H      S      H     H                                  79    4-Br     H       H      S      H     H                                  80    3-CF.sub.3                                                                             H       H      S      H     H                                  81    4-Cl     H       H      S      H     H                                  82    3-Cl     H       H      S      H     H                                  83    3-CF.sub.3                                                                             H       H      SO(α)                                                                          H     H                                  84    4-CF.sub.3                                                                             H       H      SO.sub.2                                                                             H     H                                  85    4-CF.sub.3                                                                             H       H      SO(α)                                                                          H     H                                  86    3,4-di-Cl                                                                              H       H      SO.sub.2                                                                             H     H                                  87    4-Br     H       H      SO(α)                                                                          H     H                                  88    4-Br     H       H      SO(β)                                                                           H     H                                  89    3,4-di-Cl                                                                              H       H      SO(α)                                                                          H     H                                  90    3,4-di-Cl                                                                              H       H      SO(β)                                                                           H     H                                  91    4-Cl     H       H      SO(α)                                                                          H     H                                  92    4-Cl     H       H      SO(β)                                                                           H     H                                  93    3-Cl     H       H      SO(α)                                                                          H     H                                  94    3-Cl     H       H      SO(β)                                                                           H     H                                  95    4-Br     H       H      SO.sub.2                                                                             H     H                                  96    3-CF.sub.3                                                                             H       H      SO.sub.2                                                                             H     H                                  97    4-Cl     H       H      SO.sub.2                                                                             H     H                                  98    3-Cl     H       H      SO.sub.2                                                                             H     H                                  99    3-CF.sub.3                                                                             H       H      SO(β)                                                                           H     H                                  100   4-CF.sub.3                                                                             5-Cl    H      S      H     H                                  101   3-CF.sub.3                                                                             5-Cl    H      S      H     H                                  102   4-Cl     5-Cl    H      S      H     H                                  103   3-Cl     5-Cl    H      S      H     H                                  104   4-Br     5-Cl    H      S      H     H                                  105   3,4-di-Cl                                                                              5-Cl    H      S      H     H                                  106   4-CF.sub.3                                                                             6-Cl    H      S      H     H                                  107   3-CF.sub.3                                                                             6-Cl    H      S      H     H                                  108   4-Cl     6-Cl    H      S      H     H                                  109   3-Cl     6-Cl    H      S      H     H                                  110   4-Br     6-Cl    H      S      H     H                                  111   3,4-di-Cl                                                                              6-Cl    H      S      H     H                                  112   4-CF.sub.3                                                                             5-Cl    H      SO.sub.2                                                                             H     H                                  113   3-CF.sub.3                                                                             5-Cl    H      SO.sub.2                                                                             H     H                                  114   4-Cl     5-Cl    H      SO.sub.2                                                                             H     H                                  115   3-Cl     5-Cl    H      SO.sub.2                                                                             H     H                                  116   4-Br     5-Cl    H      SO.sub.2                                                                             H     H                                  117   3,4-di-Cl                                                                              5-Cl    H      SO.sub.2                                                                             H     H                                  118   4-CF.sub.3                                                                             6-Cl    H      SO.sub.2                                                                             H     H                                  119   3-CF.sub.3                                                                             6-Cl    H      SO.sub.2                                                                             H     H                                  120   4-Cl     6-Cl    H      SO.sub.2                                                                             H     H                                  121   3-Cl     6-Cl    H      SO.sub.2                                                                             H     H                                  122   4-Br     6-Cl    H      SO.sub.2                                                                             H     H                                  123   3,4-di-Cl                                                                              6-Cl    H      SO.sub.2                                                                             H     H                                  124   4-CF.sub.3                                                                             5-Cl    H      SO(α)                                                                          H     H                                  125   4-CF.sub.3                                                                             5-Cl    H      SO(β)                                                                           H     H                                  126   3-CF.sub.3                                                                             5-Cl    H      SO(α)                                                                          H     H                                  127   3-CF.sub.3                                                                             5-Cl    H      SO(β)                                                                           H     H                                  128   4-Cl     5-Cl    H      SO(α)                                                                          H     H                                  129   4-Cl     5-Cl    H      SO(β)                                                                           H     H                                  130   3-Cl     5-Cl    H      SO(α)                                                                          H     H                                  131   3-Cl     5-Cl    H      SO(β)                                                                           H     H                                  132   4-Br     5-Cl    H      SO(α)                                                                          H     H                                  133   4-Br     5-Cl    H      SO(β)                                                                           H     H                                  134   3,4-di-Cl                                                                              5-Cl    H      SO(α)                                                                          H     H                                  135   3,4-di-Cl                                                                              5-Cl    H      SO(β)                                                                           H     H                                  136   4-CF.sub.3                                                                             6-Cl    H      SO(α)                                                                          H     H                                  137   4-CF.sub.3                                                                             6-Cl    H      SO(β)                                                                           H     H                                  138   3-CF.sub.3                                                                             6-Cl    H      SO(α)                                                                          H     H                                  139   3-CF.sub.3                                                                             6-Cl    H      SO(β)                                                                           H     H                                  140   4-Cl     6-Cl    H      SO(α)                                                                          H     H                                  141   4-Cl     6-Cl    H      SO(β)                                                                           H     H                                  142   3-Cl     6-Cl    H      SO(α)                                                                          H     H                                  143   3-Cl     6-Cl    H      SO(β)                                                                           H     H                                  144   4-Br     6-Cl    H      SO(α)                                                                          H     H                                  145   4-Br     6-Cl    H      SO(β)                                                                           H     H                                  146   3,4-di-Cl                                                                              6-Cl    H      SO(α)                                                                          H     H                                  147   3,4-di-Cl                                                                              6-Cl    H      SO(β)                                                                           H     H                                  148   4-CF.sub.3                                                                             5-Br    H      S      H     H                                  149   3-CF.sub.3                                                                             5-Br    H      S      H     H                                  150   4-Cl     5-Br    H      S      H     H                                  151   3-Cl     5-Br    H      S      H     H                                  152   4-Br     5-Br    H      S      H     H                                  153   3,4-di-Cl                                                                              5-Br    H      S      H     H                                  154   4-CF.sub.3                                                                             H       H      SO(β )                                                                          H     H                                  155   4-CF.sub.3                                                                             H       H      S      H     H                                  156   4-CF.sub.3                                                                             H       H      S      H     H                                  157   4-CF.sub.3                                                                             H       H      S      H     H                                  158   4-CF.sub.3                                                                             5-Cl    C(O)Me S      H     H                                  159   4-CF.sub.3                                                                             5-Cl    CO.sub.2 Me                                                                          S      H     H                                  160   4-CF.sub.3                                                                             5-Cl    Me     S      H     H                                  161   4-Cl     H       C(O)Me S      H     H                                  162   4-Cl     H       Me     S      H     H                                  163   4-Cl     5-Cl    C(O)Me S      H     H                                  164   4-Cl     5-Cl    Me     S      H     H                                  165   4-CF.sub.3                                                                             H       H      S      Me    Me                                 166   4-Cl     H       H      S      Me    Me                                 167   4-Br     H       H      S      Me    Me                                 168   4-Cl     5-Cl    H      S      Me    Me                                 169   4-Br     5-Cl    H      S      Me    Me                                 170   4-CF.sub.3                                                                             H       H      S      Me    H                                  171   4-CF.sub.3                                                                             H       H      S      H     Me                                 172   4-Cl     H       H      S      Me    H                                  173   4-Cl     H       H      S      H     Me                                 174   4-Br     H       H      S      Me    H                                  175   4-Br     H       H      S      H     Me                                 176   4-CF.sub.3                                                                             5-Cl    H      S      Me    H                                  177   4-CF.sub.3                                                                             5-Cl    H      S      H     Me                                 178   4-Cl     5-Cl    H      S      Me    H                                  179   4-Cl     5-Cl    H      S      H     Me                                 180   4-Br     5-Cl    H      S      Me    H                                  181   4-Br     5-Cl    H      S      H     Me                                 ______________________________________                                    

EXAMPLE 9 Fall Armyworm

Test units, each consisting of an 8-ounce plastic cup containing a layerof wheat germ diet, approximately 0.5 cm thick, were prepared. Tenthird-instar larvae of fall armyworm (Spodoptera fruqiperda) were placedinto each cup. Solutions of each of the belowlisted test compounds(acetone/distilled water 75/25 solvent) were sprayed onto the cups, asingle solution per cup. Spraying was accomplished by passing the cups,on a conveyer belt, directly beneath a flat fan hydraulic nozzle whichdischarged the spray at a rate of 0.5 pounds of active ingredient peracre (about 0.55 kg/ha) at 30 p.s.i. The cups were then covered and heldat 27° C. and 50% relative humidity for 72 hours, after which timemortality readings were taken. Of the compounds tested on fall armyworm,the following resulted in greater than or equal to 80% mortality: 3, 4,5, 7, 15, 17, 20, 22, 23, 25, 45, 59, 72, 100, 125, 148, 158, 159. 160,165, 166, 168, 169, 170, 173, 177, 179, 181.

EXAMPLE 10 European Corn Borer

Test units, each consisting of an 8-ounce plastic cup containing aone-inch square of wheat germ/soyflour diet were prepared. Fivethird-instar larvae of the European corn borer (Ostrinia nubilalis) wereplaced into each cup. The test units were sprayed as described inExample 9 with individual solutions of the below-listed compounds. Thecups were then covered and held at 27° C. and 50% relative humidity for48 hours, after which time mortality readings were taken. Of thecompounds tested on European corn borer, the following resulted ingreater than or equal to 80% mortality: 2, 3, 4, 5, 15, 22, 23, 29, 45,47, 53, 54, 55, 56, 58, 59, 71, 72, 81 84, 91, 95, 97, 100, 165, 177.

EXAMPLE 11 Southern Corn Rootworm

Test units, each consisting of an 8-ounce plastic cup containing 1sprouted corn seed, were prepared. Sets of three test units were sprayedas described in Example 9 with individual solutions of the testcompounds. After the spray on the cups had dried, five third-instarlarvae of the southern corn rootworm (Diabrotica undecimounctatahowardi) were placed into each cup. A moistened dental wick was insertedinto each cup to prevent drying and the cups were then covered. The cupswere then held at 27° C. and 50% relative humidity for 48 hours, afterwhich time mortality readings were taken. Of the compounds tested onSouthern rootworm, the following resulted in greater than or equal to80% mortality: 1, 2, 3, 4, 5, 7, 15, 16, 17, 20, 21, 22, 23, 25, 27, 29,35, 36, 45, 47, 53, 54, 56, 58, 59, 72, 76, 79, 81, 84, 91, 95, 97, 100,124, 125, 132, 133, 148, 154, 157, 158, 160, 162, 165, 166, 168, 169,170, 172, 173, 174, 175, 180.

EXAMPLE 12 Boll Weevil

Five adult boll weevils (Anthonomus orandis) were placed into each of aseries of 9-ounce cups. The test procedure employed was then otherwisethe same as in Example 9. Mortality readings were taken 48 hours aftertreatment. Of the compounds tested on boll weevil, the followingresulted in greater than or equal to 80% mortality: 1, 2, 3, 4, 5, 7,14, 15, 22, 23, 35, 45, 47, 53, 58, 59, 61, 67, 71, 72, 76, 81, 84, 91,97, 104, 165. 177.

EXAMPLE 13 Aster Leafhopper

Test units were prepared from a series of 12-ounce cups, each containingoat (Avena sativa) seedlings in a 1-inch layer of sterilized soil. Thetest units were sprayed as described in Example 9 with individualsolutions of the below-listed compounds. After the oats had dried fromthe spraying, between 10 and 15 adult aster leafhoppers (Mascrostelesfascifrons) were aspirated into each of the covered cups. The cups wereheld at 27° C. and 50% relative humidity for 48 hours, after which timemortality readings were taken. Of the compounds tested on asterleafhopper, the following resulted in greater than or equal to 80%mortality: 2, 3, 4, 5, 7, 15, 16, 20, 22, 23, 25, 45, 47, 53, 59, 72,79, 100, 104, 157, 158, 159, 160, 162, 165, 166, 168, 169, 171, 172,173, 174, 175, 177, 179, 181.

EXAMPLE 14 Tobacco Budworm

The test procedure of Example 9 was repeated on third-instar larvae ofthe tobacco budworm (Heliothis virescens) except that mortality wasassessed at 48 hours. Of the compounds tested on tobacco budworm, thefollowing resulted in greater than or equal to 80% mortality: 5, 7, 15,23, 25, 39, 100, 160, 165, 168, 177.

EXAMPLE 15 Soil Control of Southern Corn Rootworm

Test units, each consisting of a three inch cylindrical pot containing200 grams of moist sassafras loam soil and 2 kernels of Dekalb T1100corn were prepared. Spraying was accomplished by passing the pots, on aconveyer belt, directly beneath a flat fan hydraulic nozzle whichdischarged the spray at a rate of 0.25 pounds of active ingredient peracre (about 2 ppm soil concentration) at 30 p.s.i. After the test unitshad been sprayed, the corn seed was covered with soil and tenthird-instar southern corn rootworm larvae (Diabrotica undecimpunctatahowardi) were added to each unit. Test units were held at 24 degree C.,70% relative humidity and under a photo cycle of 16 hours of light/8hours of darkness for 7 days, after which time control readings weretaken. Control was measured by root injury ratings of 1 to 5, where 1was no injury and 5 was complete destruction of the root system. Percentof corn seedlings that emerged also was utilized to measure control. Theresults are tabulated below.

    ______________________________________                                        Compound     Root Rating                                                                              % Emergence                                           ______________________________________                                         2           1.5        100                                                    3           1.0        88                                                     5           1.0        100                                                   15           1.3        88                                                    20           1.6        75                                                    22           2.0        75                                                    23           1.0        75                                                    29           1.0        100                                                   59           1.1        100                                                   ______________________________________                                    

What is claimed is:
 1. A compound of the formula ##STR24## wherein##STR25## A is a 1, 2 or 3-atom bridge having 0 to 3 carbon atoms and 0to 1 oxygen atom NR₆ group, or S(O)_(q) group, wherein each carbonindividual be substituted with 1 to 2 substituents selected from 1 to 2halogen, C₁ to C₆ alkyl, C₂ to C₄ alkoxycarbonyl or phenyl optionallysubstituted with 1 to 3 substituents selected from W and one of thecarbon atoms can be C(O) or C(S);B is H C₁ to C₆ alkyl, C₁ to C₆haloalkyl, C₂ to C₆ alkenyl, C₂ to C₆ haloalkenyl, C₂ to C₆ alkynyl,OR₇, C₂ to C₆ alkoxyalkyl, C₂ to C₆ cyanoalkyl, C₃ to C₈alkoxycarbonylalkyl, CO₂ R₃, C(O)R₃, C(O)NR₃ R₄, C(S)NR₃ R₄, C(S)R₃,C(S)SR₃, phenyl, phenyl substituted by (R₅)_(p), benzyl, or benzylsubstituted with 1 to 3 substituents independently selected from W; J isH, C₁ to C₄ alkyl or phenyl optionally substituted with W; K is H or CH₃; W is halogen, CN, NO₂, C₁ to C₂ alkyl, C₁ to C₂ haloalkyl, C₁ to C₂alkoxy, C₁ to C₂ haloalkoxy, C₁ to C₂ alkylthio, C₁ to C₂ haloalkylthio,C₁ to C₂ alkylsulfonyl or C₁ to C₂ haloalkylsulfonyl; R₁, R₂ and R₅ areindependently R₃, halogen, CN, N₃, SCN, NO₂, OR₃, SR₃, SOR₃, SO₂ R₃,OC(O)R₃, OSO₂ R₃, CO₂ R₃, C(O)R₃, C(O)NR₃ R₄, SO₂ NR₃ R₄, NR₃ R₄, NR₄C(O)R₃, OC(O)NHR₃, NR₄ C(O)NHR₃, NR₄ SO₂ R₃, or when m, n or p is 2, R₁,R₂ or R₅ can be taken together to form a 5 or 6 membered fused ring as--OCH₂ O--, --OCH₂ CH₂ O--, or --CH₂ CH₂ O--, each of which can besubstituted with 1 to 4 halogen atoms or 1 to 2 methyl groups: R₃ is H,C₁ to C₆ alkyl, C₁ to C₆ haloalkyl, C₂ to C₆ alkenyl, C₂ to C₆haloalkenyl, C₂ to C₆ alkynyl, C₂ to C₆ haloalkynyl, C₂ to C₆alkoxyalkyl, C₂ to C₆ alkylthioalkyl, C₁ to C₆ nitroalkyl, C₂ to C₆cyanoalkyl, C₃ to C₈ alkoxycarbonylalkyl, C₃ to C₆ cycloalkyl, C₃ to C₆halocycloalkyl, phenyl, benzyl, or phenyl or benzyl substituted with 1to 3 substituents independently selected from W; R₄ is H, C₁ to C₄ alkylor R₃ and R₄ can be taken together as (CH₂)₄, (CH₂)₅ or (CH₂ CH₂ OCH₂CH₂); R₆ is H, C₁ to C₄ alkyl, C₁ to C₄ haloalkyl, C₂ to C₄ alkenyl, C₂to C₄ haloalkenyl, phenyl, benzyl, phenyl optionally substituted with Wor benzyl optionally substituted with W; R₇ is H, C₁ to C₄ alkyl, C₂ toC₄ alkenyl, C₂ to C₄ alkynyl, C₂ to C₄ alkylcarbonyl, C₂ to C₄alkoxycarbonyl, C₁ to C₄ alkylsulfonyl; X is O or S; n is 1 to 4; m is 1to 5; p is 1 to 3; q is 0 to 2; and Y i H, C₁ to C₆ alkyl, benzyl, C₂ toC₆ alkoxyalkyl, CHO, C₂ to C₆ alkylcarbonyl, C₂ to C₆ alkoxycarbonyl, C₂to C₆ haloalkylcarbonyl, C₁ to C₆ alkylthio, C₁ to C₆ haloalkylthio,phenylthio, or phenylthio substituted with 1 to 3 substituentsindependently selected from W.
 2. A compound according to claim 1wherein Q is ##STR26## X is O or S; X¹ is O or S;t is 0, 1 or 2; V is O,S(O)_(q), or NR₆ ; Z is O or NR₆ ; R₈ is H, halogen, C₁ -C₆ alkyl, C₂-C₄ alkoxycarbonyl, phenyl or phenyl substituted by 1--3 substituentsselected from W; and g is 0, 1 or
 2. 3. A compound according to claim 2wherein B is H, C₁ to C₆ alkyl, C₁ to C₆ haloalkyl, C₂ to C₆ alkenyl, C₂to C₆ alkynyl, C₂ to C₆ alkoxyalkyl, C₃ to C₈ alkoxycarbonylalkyl, CO₂R₃, C(O)R₃, C(O)NR₃ R₄, C(S)NR₃ R₄, C(S)R₃, C(S)SR₃, phenyl or phenylsubstituted by (R₅)_(p) ;J is H or CH₃ ; R₃ is H, C₁ to C₄ alkyl, C₁ toC₂ haloalkyl, C₃ to C₄ alkenyl, C₃ to C₄ haloalkenyl, propargyl, phenyl,benzyl, or phenyl or benzyl substituted with one of F, Cl, Br, CF₃ orNO₂ ; R₆ is H, C₁ to C₄ alkyl, allyl or propargyl; n is 1 or 2; p is 1or 2; m is 1 to 3; and Y is H, C₁ to C₄ alkyl, SCH₃, SCCL₃, SO₂ CH₃, SC₆H₅, 2--NO₂ --C₆ H₄ S, C(O)CH₃, C(O)CF₃, CO₂ CH₃ or CO₂ CH₂ CH₃.
 4. Acompound according to claim 3 wherein B is H, C₁ to C₄ alkyl, C₃ -C₄alkoxycarbonylalkyl, CO₂ R₃, C(O)R₃, phenyl or phenyl substituted by(R₅)_(p) ;J is H; K is H; R₁ is H, halogen, CN, SCN, NO₂, OR₃, SR₃, SO₂R₃, CO₂ R₃, C(O)R₃ or R₃ with one R₁ substituent in the 4-position, orwhen m is 2 then R₁ can be taken together as --CH₂ C(CH₃)₂ O--, OCH₂ CH₂O--, OCF₂ CF₂ O-- or --CF₂ CF₂ O-- to form a 5 or 6 membered fused ring;R₂ and R₅ are H, R₃, halogen, CN, SCN, NO₂, OR₃, SR₃, SO₂ R₃, OC(O)R₃,OSO₂ R₃, CO₂ R₃, C(O)R₃, C(O)NR₃ R₄, SO₂ NR₃ R₄ or NR₃ R₄ ; R₃ is C₁ -C₄alkyl, C₁ -C₂ haloalkyl, C₃ -C₄ alkenyl or propargyl; R₄ and R₈ are H orCH₃ ; X is O; X' is 0; m is 1 or 2; t is 1; and q is
 0. 5. A compoundaccording to claim 4 wherein R₁ is Cl, F, Br, CF₃, CN, OCF₃, OCF₂ H orSCF₂ H; R₂ is H, Cl, F, Br, CN, CF₃, CH₃, OCF₂ H, OCF₃, SCH₃, SCF₂ H,SO₂ CH₃ or NO₂ ;R₆ is H or CH₃ ; B is H, CH₃, CH₂ CH₃, CO₂ CH₃, CO₂ CH₂CH₃, phenyl or phenyl substituted by halogen, CN, CF₃ or NO₂, and; Y isH.
 6. A compound according to claim 5 wherein Q is Q-1.
 7. A compoundaccording to claim 5 wherein Q is Q-`.
 8. A compound according to claim6: methyl3,3a,4,5-tetrahydro-2-[[4(trifluoromethyl)phenylamino]carbonyl]2H-benz[g]indazole-3a-carboxylate.9. A compound according to claim 6: methyl7-chloro-3,3a,4,5-tetrahydro-2-[[4trifluoromethyl)phenylamino]carbonyl]2H-benz[g]indazole-3a-carboxylate.10. A compound according to claim 6:7-chloro-3,3a,4,-tetrahydro-N-[4-(trifluoromethyl)phenyl]-2H-benz[g]indazole-2carboxamide.11. A compound according to claim 6: methyl6-fluoro-3,3a,4,5-tetrahydro-2-[[4(trifluoromethyl)phenylamino]carbonyl]-2Hbenz[g]indazole-3a-carboxylate.12. A composition comprising an insecticidally effective amount of acompound according to any one of claims 1 to 11 and an agriculturallysuitable carrier therefor.
 13. A method for controlling insectscomprising contacting them with an insecticidially effective amount of acompound according to any one of claims 1 to 11.